Hexanophenone (1-Phenyl-1-hexanone) [C12H16O]

Query Query

Results

Date

146 reactions in Reaxys

2018-05-06 22h:31m:25s (UTC)

O

1. Query

Search as: Product, As drawn, No mixtures ) AND (IDE.XRN=1908667))

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

1/62

2018-05-06 22:32:29

O

O

Rx-ID: 9188500 View in Reaxys 1/146 Yield

Conditions & References With palladium (II) nitrate, 2-amino-phenol in 1,4-dioxane, Time= 5h, T= 120 °C Shimada, Tomohiro; Yamamoto, Yoshinori; Journal of the American Chemical Society; vol. 124; nb. 43; (2002); p. 12670 12671 View in Reaxys

30 %Chromat., 35 %Chromat.

Stage 1: With AuP(t-Bu)3(N-trifluoromethanesulfonyl)2, glycerol in acetonitrile, Time= 24h, T= 80 °C , Inert atmosphere Stage 2: With hydrogenchloride, water in acetonitrile, Time= 24h, T= 80 °C , Inert atmosphere Corma, Avelino; Ruiz, Violeta R.; Leyva-Perez, Antonio; Sabater, Maria J.; Advanced Synthesis and Catalysis; vol. 352; nb.

10; (2010); p. 1701 - 1710 View in Reaxys With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I), copper(II) bis(trifluoromethanesulfonate) in tetrahydrofuran, water, Time= 16h, T= 120 °C , Sealed tube Fang, Weizhen; Presset, Marc; Guerinot, Amandine; Bour, Christophe; Bezzenine-Lafollee, Sophie; Gandon, Vincent; Chemistry - A European Journal; vol. 20; nb. 18; (2014); p. 5439 - 5446 View in Reaxys With C47H41AuBF15N2S in 1,4-dioxane, water, Time= 18h, T= 80 °C , Meyer-Schuster Rearrangement, Overall yield = 100 percent; regioselective reaction Weerasiri, Kushan C.; Chen, Danmin; Wozniak, Derek I.; Dobereiner, Graham E.; Advanced Synthesis and Catalysis; vol.

358; nb. 24; (2016); p. 4106 - 4113 View in Reaxys

11 Stage 1: With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I), Triphenylphosphine oxide in water, toluene, %Spectr., Time= 0.0833333h, T= 20 °C , Inert atmosphere 28 %Spectr. Stage 2: With silver trifluoromethanesulfonate in water, toluene, Time= 1h, T= 50 °C , Inert atmosphere, regioselective reaction Endo, Naoki; Inoue, Mami; Iwasawa, Tetsuo; European Journal of Organic Chemistry; vol. 2018; nb. 9; (2018); p. 1136 1140 View in Reaxys

O

Rx-ID: 10289688 View in Reaxys 2/146 Yield 99 %

Conditions & References With iron(III) chloride, water, silver(I) triflimide in 1,4-dioxane, Time= 60h, T= 95 °C , regioselective reaction Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino; Chemistry - A European Journal; vol. 18; nb. 35; (2012); p. 11107 - 11114

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/62

2018-05-06 22:32:29

View in Reaxys 89 %

With toluene-4-sulfonic acid in ethanol, Time= 0.5h, T= 170 °C , microwave irradiation Le Bras, Gaelle; Provot, Olivier; Peyrat, Jean-Francois; Alami, Mouad; Brion, Jean-Daniel; Tetrahedron Letters; vol. 47; nb. 31; (2006); p. 5497 - 5501 View in Reaxys

89 %

With water, toluene-4-sulfonic acid in ethanol, Time= 0.5h, T= 170 °C , Microwave irradiation, regioselective reaction Jacubert, Maud; Provot, Olivier; Peyrat, Jean-Francois; Hamze, Abdallah; Brion, Jean-Daniel; Alami, Mouad; Tetrahedron; vol. 66; nb. 21; (2010); p. 3775 - 3787 View in Reaxys

83 %

General procedure for hydration of alkynes General procedure: Reactions were performed in a magnetically stirred round bot-tomed flask fitted with a condenser and placed in a temperature controlled oil bath. Zeolite (H) (100 mg) was added to the well stirred solution of alkyne (2 mmol) and H2O (8 mmol) and the reac-tion mixture was allowed to stir at 100 °C. After disappearance of the alkyne (monitored by TLC) or after an appropriate time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate. The catalyst was separated by filtration and the removal of solvent in vacuo yielded residue. and it was further puri-fied by column chromatography using silica gel (100–200 mesh) to afford pure products. All the products were identified on the basisof H1 and C13NMR spectral data.

With water in neat (no solvent), Time= 24h, T= 100 °C , Green chemistry, regioselective reaction Mameda, Naresh; Peraka, Swamy; Marri, Mahender Reddy; Kodumuri, Srujana; Chevella, Durgaiah; Gutta, Naresh; Nama, Narender; Applied Catalysis A: General; vol. 505; (2015); p. 213 - 216; Art.No: 15488 View in Reaxys

25 %

With tetrafluoroboric acid in chloroform-d1, water, Time= 1h, T= 60 °C , Reagent/catalyst, Time La Sorella, Giorgio; Sperni, Laura; Ballester, Pablo; Strukul, Giorgio; Scarso, Alessandro; Catalysis Science and Technology; vol. 6; nb. 15; (2016); p. 6031 - 6036 View in Reaxys With butan-1-ol in dichloromethane, Time= 24h, T= 20 °C Corma, Avelino; Ruiz, Violeta R.; Leyva-Perez, Antonio; Sabater, Maria J.; Advanced Synthesis and Catalysis; vol. 352; nb.

10; (2010); p. 1701 - 1710 View in Reaxys With water in 1,4-dioxane, Time= 6h, T= 110 °C , regioselective reaction Cabrero-Antonino, Jose R.; Tejeda-Serrano, María; Quesada, Manuel; Vidal-Moya, Jose A.; Leyva-Pérez, Antonio; Corma, Avelino; Chemical Science; vol. 8; nb. 1; (2016); p. 689 - 696 View in Reaxys With trifluorormethanesulfonic acid, water in 2,2,2-trifluoroethanol, Time= 48h, T= 40 °C , Inert atmosphere Liu, Sensheng; Liu, Huan; Zhou, Haifeng; Liu, Qixing; Lv, Jinliang; Organic Letters; vol. 20; nb. 4; (2018); p. 1110 - 1113 View in Reaxys

10 %Spectr. Stage 1: in water, toluene, Time= 0.0833333h, T= 20 °C , Inert atmosphere Stage 2: With silver trifluoromethanesulfonate in water, toluene, Time= 1h, T= 50 °C , Inert atmosphere, regioselective reaction Endo, Naoki; Inoue, Mami; Iwasawa, Tetsuo; European Journal of Organic Chemistry; vol. 2018; nb. 9; (2018); p. 1136 1140 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/62

2018-05-06 22:32:29

NH

O

Rx-ID: 47197831 View in Reaxys 3/146 Yield

Conditions & References With hydrogenchloride, water, Time= 0.5h, T= 100 °C Rodríguez-Álvarez, María J.; García-Álvarez, Joaquín; Uzelac, Marina; Fairley, Michael; O'Hara, Charles T.; Hevia, Eva; Chemistry - A European Journal; vol. 24; nb. 7; (2018); p. 1720 - 1725 View in Reaxys

OH O

O

Rx-ID: 716326 View in Reaxys 4/146 Yield 88 %

Conditions & References With potassium phosphate, aluminum oxyhydroxide, palladium in toluene, Time= 12h, T= 110 °C Kwon, Min Serk; Kim, Namdu; Seo, Seong Hyeok; Park, In Soo; Cheedrala, Ravi Kumar; Park, Jaiwook; Angewandte Chemie - International Edition; vol. 44; nb. 42; (2005); p. 6913 - 6915 View in Reaxys

84 %

15 : 1-phenylhexan-1-one Acetophenone (120mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1.0molpercent), cesium carbonate (33mg, 0.1mmol,0.1equiv.), N-butanol (82mg, 1.1mmol) and tert-amyl alcohol (1ml) were sequentially added to a 5mL round bottomed flask. ReactionAfter the reaction mixture was refluxed in air for six hours, cooled to room temperature. The solvent is removed by rotary evaporation, then purified by column chromatography (developing solvent:Petroleum ether / ethyl acetate) to give pure target compound, yield: 84percent With C16H14IrN2O3, caesium carbonate in tert-Amyl alcohol, Time= 6h, Reflux Patent; Nanjing University of Science and Technology; Ma, Juan; Li, Lei; Li, Feng; (17 pag.); CN105439787; (2016); (A) Chinese View in Reaxys

80 %

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], potassium hydoxide, Time= 0.166667h, T= 110 °C , Inert atmosphere, Aldol Condensation Li, Jian; Zhang, Weixing; Wang, Feng; Jiang, Min; Dong, Xiaochun; Zhao, Weili; Chinese Journal of Chemistry; vol. 30; nb. 10; (2012); p. 2363 - 2366,4 View in Reaxys

72 %

With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br, caesium carbonate in tert-Amyl alcohol, Time= 22h, T= 140 °C , Inert atmosphere Peña-López, Miguel; Piehl, Patrick; Elangovan, Saravanakumar; Neumann, Helfried; Beller, Matthias; Angewandte Chemie - International Edition; vol. 55; nb. 48; (2016); p. 14967 - 14971; Angew. Chem.; vol. 128; nb. 48; (2016); p. 15191 15195,5 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/62

2018-05-06 22:32:29

70 %

With potassium hydroxide, 1-dodecene, tris(triphenylphosphine)ruthenium(II) chloride in 1,4-dioxane, Time= 20h, T= 80 °C Cho, Chan Sik; Kim, Bok Tae; Kim, Tae-Jeong; Chul Shim, Sang; Tetrahedron Letters; vol. 43; nb. 44; (2002); p. 7987 7989 View in Reaxys

65 %

With lithium tert-butoxide in toluene, Time= 12h, T= 110 °C , Inert atmosphere Liang, Yu-Feng; Zhou, Xin-Feng; Tang, Shi-Ya; Huang, Yao-Bing; Feng, Yi-Si; Xu, Hua-Jian; RSC Advances; vol. 3; nb.

21; (2013); p. 7739 - 7742 View in Reaxys

53 %

4.4. General procedure for α-alkylation of ketones with alcohols General procedure: To a solution of Ir(III) complex (0.02 mmol) and base (1.0 mmol) in solution (3 mL) was added the corresponding ketone (1.0 mmol) and alcohol (2.0 mmol) under nitrogen. The reaction mixture was then placed in an oil bath and heated at 110 °C for 12 h, cooled and quenched with water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate, then the combined organic layers were washed with water, dried over MgSO4, filtered, and the solvent was removed on a rotary evaporator. The resulting residue was purified by flash chromatography on silica gel using suitable mixtures of hexane/ethyl acetate as eluent. The products were characterized by comparing their m.p., IR and 1 H NMR spectra with those found in the literature [8], [12], [15], [32] and [33].

With C52H43Cl2IrN2P2, sodium hydroxide in 1,4-dioxane, Time= 12h, T= 110 °C , Inert atmosphere Xu, Chen; Dong, Xin-Ming; Wang, Zhi-Qiang; Hao, Xin-Qi; Li, Zhen; Duan, Lu-Meng; Ji, Bao-Ming; Song, Mao-Ping; Journal of Organometallic Chemistry; vol. 700; (2012); p. 214 - 218 View in Reaxys

37 %

With C19H37NO3P2Re(1+)*Br(1-), caesium carbonate in tert-Amyl alcohol, Time= 22h, T= 140 °C , Inert atmosphere, Sealed tube Piehl, Patrick; Peña-López, Miguel; Frey, Anna; Neumann, Helfried; Beller, Matthias; Chemical Communications; vol. 53; nb. 22; (2017); p. 3265 - 3268 View in Reaxys

32 %

General procedure for the [RuCl2(α6-p-cymene)]2/L1-catalyzed α-alkylation of ketones with alcohols General procedure: Cs2CO3 (0.6 mmol,195.6 mg) and toluene (1 mL) were added to a Schlenk tube under a N2 atmosphere.

[RuCl2(η6-p-cymene)]2 (0.005 mmol, 3.1 mg), L1 (0.01 mmol, 2.8 mg), alcohols (1.1 mmol) and ketones (1.0 mmol) were added in that order and the Schlenk tube was closed and stirred at 120°C for 18 h. The reaction mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate (20 mL x 3). The combined extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by column chromatography using petroleum ether/ethyl acetate as eluent to give the corresponding product (Figs. S22-S47 in Supporting Information).

With [Ru(η6-p-cymene)Cl2]2, caesium carbonate, 2-((diphenylphosphino)amido)pyridine in toluene, Time= 18h, T= 120 °C , Schlenk technique, Inert atmosphere Liu, Shi-Yuan; Xu, Lin-Yan; Liu, Chun-Yu; Ren, Zhi-Gang; Young, David James; Lang, Jian-Ping; Tetrahedron; vol. 73; nb. 17; (2017); p. 2374 - 2381 View in Reaxys With aluminum oxide, T= 250 °C Ohta; Kogyo Kagaku Zasshi; vol. 52; (1949); p. 162; ; (1951); p. 3324 View in Reaxys

91 % Chromat.

With sodium hydroxide, bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] in toluene, Time= 17h, T= 110 °C Fujita, Ken-Ichi; Asai, Chiho; Yamaguchi, Tetsuhiro; Hanasaka, Fumihiro; Yamaguchi, Ryohei; Organic Letters; vol. 7; nb. 18; (2005); p. 4017 - 4019 View in Reaxys With potassium hydroxide, bis(1,5-cyclooctadiene)diiridium(I) dichloride, triphenylphosphine, Time= 4h, T= 100 °C Onodera, Gen; Nishibayashi, Yoshiaki; Uemura, Sakae; Angewandte Chemie - International Edition; vol. 45; nb. 23; (2006); p. 3819 - 3822 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/62

2018-05-06 22:32:29

93 %Chromat.

With potassium phosphate tribasic trihydrate, 5-palladium/activated carbon in water, Time= 1.5h, T= 180 °C , Microwave irradiation, Temperature, Reagent/catalyst Xu, Guoqiang; Li, Qiong; Feng, Jiange; Liu, Qiang; Zhang, Zuojun; Wang, Xicheng; Zhang, Xiaoyun; Mu, Xindong; ChemSusChem; vol. 7; nb. 1; (2014); p. 105 - 109 View in Reaxys

OH

OH HO

O

Rx-ID: 10073882 View in Reaxys 5/146 Yield 88 %

Conditions & References With sodium t-butanolate, bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] in toluene, Time= 17h, T= 110 °C Fujita, Ken-Ichi; Asai, Chiho; Yamaguchi, Tetsuhiro; Hanasaka, Fumihiro; Yamaguchi, Ryohei; Organic Letters; vol. 7; nb. 18; (2005); p. 4017 - 4019 View in Reaxys

9 %, 83 %

With tris-(dibenzylideneacetone)dipalladium(0), 2Br(1-)*C30H47BrN4 (2+), hydrogen, sodium hydroxide in para-xylene, Time= 24h, T= 125 °C , p= 760.051Torr Kose, Osamu; Saito, Susumu; Organic and Biomolecular Chemistry; vol. 8; nb. 4; (2010); p. 896 - 900 View in Reaxys

74 %

With C28H26ClN6Ru(1+)*F6P(1-), sodium isopropylate in toluene, Time= 3h, T= 125 °C , Schlenk technique, Inert atmosphere, Sealed tube, Glovebox, Green chemistry Shee, Sujan; Paul, Bhaskar; Panja, Dibyajyoti; Roy, Bivas Chandra; Chakrabarti, Kaushik; Ganguli, Kasturi; Das, Ayan; Das, Gourab Kanti; Kundu, Sabuj; Advanced Synthesis and Catalysis; vol. 359; nb. 22; (2017); p. 3888 - 3893 View in Reaxys

20 % Chromat., 60 % Chromat.

With sodium t-butanolate, bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] in toluene, Time= 17h, T= 110 °C Fujita, Ken-Ichi; Asai, Chiho; Yamaguchi, Tetsuhiro; Hanasaka, Fumihiro; Yamaguchi, Ryohei; Organic Letters; vol. 7; nb. 18; (2005); p. 4017 - 4019 View in Reaxys With [(terpy)Ru(PPh3)Cl2], potassium hydoxide in toluene, Time= 4h, Reflux, in air Gnanamgari, Dinakar; Leung, Chin Hin; Schley, Nathan D.; Hilton, Sheena T.; Crabtree, Robert H.; Organic and Biomolecular Chemistry; vol. 6; nb. 23; (2008); p. 4442 - 4445 View in Reaxys

8 %Spectr., With C29H39Cl2IrN2, potassium hydoxide in toluene, Time= 8h, T= 100 °C , Sealed tube 91 %Spectr.

Segarra, Candela; Mas-Marza, Elena; Mata, Jose A.; Peris, Eduardo; Advanced Synthesis and Catalysis; vol. 353; nb.

11-12; (2011); p. 2078 - 2084 View in Reaxys With [Ir(NCCH3)(1,5-cyclooctadiene)((1-methylimidazolyl)(2-methoxybenzyl))][BF4], caesium carbonate in toluene, Time= 10h, T= 110 °C , Inert atmosphere, Reagent/catalyst Jiménez, M. Victoria; Fernández-Tornos, Javier; Modrego, F. Javier; Pérez-Torrente, Jesús J.; Oro, Luis A.; Chemistry A European Journal; vol. 21; nb. 49; (2015); p. 17877 - 17889 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/62

2018-05-06 22:32:29

88 %Spectr. With trans-RuCl(2-(2-pyridyl-6-ol)-1,10-phenanthroline)(PPh3)2PF6, sodium hydroxide in toluene, Time= 4h, T= 125 °C , Schlenk technique, Glovebox, Inert atmosphere, Catalytic behavior Chakrabarti, Kaushik; Paul, Bhaskar; Maji, Milan; Roy, Bivas Chandra; Shee, Sujan; Kundu, Sabuj; Organic and Biomolecular Chemistry; vol. 14; nb. 46; (2016); p. 10988 - 10997 View in Reaxys With [(6,6’-dihydroxy-2,2’-bipyridine)Ru(H)(CO)(PPh3)2]Cl, potassium tert-butylate in toluene, Time= 4h, T= 130 °C , Inert atmosphere, Schlenk technique Roy, Bivas Chandra; Chakrabarti, Kaushik; Shee, Sujan; Paul, Subhadeep; Kundu, Sabuj; Chemistry - A European Journal; vol. 22; nb. 50; (2016); p. 18147 - 18155 View in Reaxys

Cl

O

O

Rx-ID: 651165 View in Reaxys 6/146 Yield 82.3 %

Conditions & References 3 : 1-phenylhexan-1-one(XIII-1) In a three-necked flask, 2.5 g (169.1 mmol) of AlCl32,10 ml of benzene (112.7 mmol),20 ml CH? Cl?With stirring,17.5 ml (112.7 mmol) of hexanoyl chloride was added dropwise,Maintaining the temperature at 0-5 ° C,Plus completed,Room temperature reaction 0.5h,Poured into ice water,Ethyl acetate was extracted three times (150 x 3)Saturated NaCl solution was washed once,Dried over anhydrous magnesium sulfate,filter,concentrate,To give 17.65 g of a light yellow oil,Yield 82.3percent.

With aluminum (III) chloride in dichloromethane, Time= 0.5h, T= 0 - 20 °C Patent; Hefei Industrial Pharmaceutical Institute Co., Ltd.; China Pharmaceutical University; NANJING MEDICAL INDUSTRY MEDICAL TECHNOLOGY CO LTD;; Xu, Yungen; Liu, Wei; He, Guangwei; Yang, Yun; Bian, Xueguo; (9 pag.); CN103408501; (2016); (B) Chinese View in Reaxys

60 %

With hafnium trifluoromethanesulfonate, trifluorormethanesulfonic acid, Time= 8h, T= 80 °C Kobayashi, Shu; Iwamoto, Shunsuke; Tetrahedron Letters; vol. 39; nb. 26; (1998); p. 4697 - 4700 View in Reaxys

58 %

With aluminium trichloride, Time= 10h, Heating, Friedel-Crafts reaction Bhattacharya, Santanu; Subramanian, Marappan; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4203 - 4206 View in Reaxys With aluminium trichloride Simon; Bulletin des Societes Chimiques Belges; vol. 38; (1929); p. 50; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2520 View in Reaxys With carbon disulfide, aluminium trichloride Schroeter; Chemische Berichte; vol. 40; (1907); p. 1603; Chemische Berichte; vol. 41; (1908); p. 7 View in Reaxys With mesoporous carbon nitride in n-heptane, Time= 20h, T= 90 °C , Friedel-Crafts acylation Goettmann, Frederic; Fischer, Anna; Antonietti, Markus; Thomas, Arne; Angewandte Chemie - International Edition; vol.

45; nb. 27; (2006); p. 4467 - 4471 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

7/62

2018-05-06 22:32:29

With aluminum (III) chloride Zygadlo; Dardas; Nowicka; Hofmann; Galewski; Molecular Crystals and Liquid Crystals; vol. 509; nb. 1; (2009); p. 283 291 View in Reaxys

OH

O

OH

HO O

Rx-ID: 37574023 View in Reaxys 7/146 Yield

Conditions & References

20 %Chro- With cis,cis,trans-[RuCl2{η2-(P,N)-2-Ph2PC6H4CH=NOH}2], potassium hydoxide in toluene, Time= 3h, T= 120 °C , Sealed tube, mat., 6 Inert atmosphere %Chromat., 60 % Francos, Javier; Menéndez-Rodríguez, Lucía; Tomás-Mendivil, Eder; Crochet, Pascale; Cadierno, Victorio; RSC Advances; vol. 6; nb. 45; (2016); p. 39044 - 39052 View in Reaxys 19 %Chromat., 20 %Chromat., 8 %Chromat.

With ruthenium-carbon composite, sodium dodecyl-sulfate, lithium hydroxide in water, T= 140 °C , Inert atmosphere, Microwave irradiation Xu, Guoqiang; Li, Qiong; Feng, Jiange; Liu, Qiang; Zhang, Zuojun; Wang, Xicheng; Zhang, Xiaoyun; Mu, Xindong; ChemSusChem; vol. 7; nb. 1; (2014); p. 105 - 109 View in Reaxys

OH

O

Rx-ID: 43919544 View in Reaxys 8/146 Yield 80 %

Conditions & References 14 : 1-phenylhexan-1-one The [(IPr) AuCl] (6mg, 0.01mmol, 1molpercent), AgOTf (2.6mg, 0.01mmol, 1molpercent), phenylacetylene (102mg, 1mmol), 1,4- dioxane (1ml) and water (36ul, 2equiv.) were successively added to 5ml microwave tube.After the reaction mixture was microwaved at 120 reactor for one hour, cooled to room temperature.Thereto was added [Cp * IrCl2]2(8mg, 0.01mmol, 1molpercent), potassium tert-butoxide (34mg, 0.3mmol, 0.3equiv.), N-butanol (148mg, 2mmol).After the reaction mixture was microwaved at 130 reactor and then reacted for 2 hours, cooled to room temperature.Filtered, and solvent was removed by rotary evaporation, then purified by column chromatography (developing solvent: petroleum ether / ethyl acetate) to give the pure title compound Yield: 80percent Stage 1: With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I), water, silver trifluoromethanesulfonate in 1,4dioxane, Time= 1h, T= 120 °C , Microwave irradiation Stage 2: With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], potassium tert-butylate in 1,4-dioxane, Time= 2h, T= 130 °C , Microwave irradiation

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/62

2018-05-06 22:32:29

Patent; Nanjing University of Science and Technology; Li, Feng; Ma, Juan; Qu, panpan; (15 pag.); CN104557500; (2016); (B) Chinese View in Reaxys

O I

I (v2)

O

Zn

(v2)

Zn

O

Rx-ID: 44134799 View in Reaxys 9/146 Yield 55 %

Conditions & References With Wilkinson's catalyst, hydrogen in tetrahydrofuran, T= 25 °C , p= 760.051Torr Maazaoui, Radhouan; Pin-Nó, María; Gervais, Kevin; Abderrahim, Raoudha; Ferreira, Franck; Perez-Luna, Alejandro; Chemla, Fabrice; Jackowski, Olivier; European Journal of Organic Chemistry; vol. 2016; nb. 34; (2016); p. 5732 - 5737 View in Reaxys

I

O

O

Rx-ID: 9018176 View in Reaxys 10/146 Yield 88 %

Conditions & References 2.7 Catalytic activity of 1a and 1b in acylation reaction General procedure: Aryl halides (2mmol) and aldehydes (2.4mmol) in 1, 4 - dioxane (20cm3) were mixed together. The base cesium carbonate (6mmol) and the respective catalyst (0.004mmol) in dichloromethane (5cm3) were then added to the solution and stirred at 100°C. The reactions were monitored by TLC and the products were isolated by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were characterized by 1H NMR, 13C NMR and melting point determination followed by their comparison with the standard literature data.

With C20H19Cl2PPdS, caesium carbonate in 1,4-dioxane, dichloromethane, Time= 16h, T= 100 °C , Reagent/catalyst Saikia, Kokil; Dutta, Dipak Kumar; Journal of Molecular Catalysis A: Chemical; vol. 408; (2015); p. 20 - 25; Art.No: 9557 View in Reaxys

43 %

With dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II), zinc in tetrahydrofuran, Time= 36h, T= 110 °C Huang, Yi-Chun; Majumdar, Kanak Kanti; Cheng, Chien-Hong; Journal of Organic Chemistry; vol. 67; nb. 5; (2002); p.

1682 - 1684 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

9/62

2018-05-06 22:32:29

Br

O

O

Rx-ID: 28159748 View in Reaxys 11/146 Yield 84 %

Conditions & References With pyrrolidine, 1,3-bis-(diphenylphosphino)propane, bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide, Time= 6h, T= 115 °C , Molecular sieve, Heck reaction Ruan, Jiwu; Saidi, Ourida; Iggo, Jonathan A.; Xiao, Jianliang; Journal of the American Chemical Society; vol. 130; nb. 32; (2008); p. 10510 - 10511 View in Reaxys

82 %

2.7 Catalytic activity of 1a and 1b in acylation reaction General procedure: Aryl halides (2mmol) and aldehydes (2.4mmol) in 1, 4 - dioxane (20cm3) were mixed together. The base cesium carbonate (6mmol) and the respective catalyst (0.004mmol) in dichloromethane (5cm3) were then added to the solution and stirred at 100°C. The reactions were monitored by TLC and the products were isolated by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were characterized by 1H NMR, 13C NMR and melting point determination followed by their comparison with the standard literature data.

With C20H19Cl2PPdS, caesium carbonate in 1,4-dioxane, dichloromethane, Time= 16h, T= 100 °C , Reagent/catalyst Saikia, Kokil; Dutta, Dipak Kumar; Journal of Molecular Catalysis A: Chemical; vol. 408; (2015); p. 20 - 25; Art.No: 9557 View in Reaxys With pyrrolidine, C21H28I3IrN6Pd, tetrabutylammomium bromide in N,N-dimethyl-formamide, Time= 16h, T= 115 °C , Inert atmosphere, Schlenk technique, Molecular sieve, Reagent/catalyst Gonell, Sergio; Poyatos, MacArena; Mata, Jose A.; Peris, Eduardo; Organometallics; vol. 31; nb. 15; (2012); p. 5606 5614,9 View in Reaxys

O

Rx-ID: 29371928 View in Reaxys 12/146 Yield 51 %

Conditions & References With tert.-butylhydroperoxide, copper(l) iodide, N-(4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)benzyl)-1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine, sodium dodecyl-sulfate in water, Time= 1h, T= 20 °C , Green chemistry, regioselective reaction Ang, Wei Jie; Lam, Yulin; Organic and Biomolecular Chemistry; vol. 13; nb. 4; (2015); p. 1048 - 1052 View in Reaxys

42 %

With pyridine, tert.-butylhydroperoxide, iodine in water, T= 80 °C , chemoselective reaction Zhang, Jintang; Wang, Zhentao; Wang, Ye; Wan, Changfeng; Zheng, Xiaoqi; Wang, Zhiyong; Green Chemistry; vol. 11; nb. 12; (2009); p. 1973 - 1978 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/62

2018-05-06 22:32:29

41 %

With tert.-butylhydroperoxide, copper(l) iodide, dimethyl 3-methyl-9-oxo-7-(4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)benzyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate in water, Time= 12h, T= 20 °C , Green chemistry Ang, Wei Jie; Chng, Yong Sheng; Lam, Yulin; RSC Advances; vol. 5; nb. 99; (2015); p. 81415 - 81428 View in Reaxys

OH HO

O

O

Rx-ID: 37574022 View in Reaxys 13/146 Yield 30 %Spectr., 55 %

Conditions & References With tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron, caesium carbonate, triphenylphosphine in toluene, Time= 48h, T= 140 °C , Inert atmosphere, Schlenk technique, Sealed tube, Green chemistry Elangovan, Saravanakumar; Sortais, Jean-Baptiste; Beller, Matthias; Darcel, Christophe; Angewandte Chemie - International Edition; vol. 54; nb. 48; (2015); p. 14483 - 14486; Angew. Chem.; vol. 127; nb. 48; (2015); p. 14691 - 14694,4 View in Reaxys

38 %Chromat., 14 %Chromat.

With [2,2]bipyridinyl, rhodium(III) chloride, sodium hydroxide in water, T= 110 °C , Inert atmosphere, Microwave irradiation, Reagent/catalyst, Temperature Xu, Guoqiang; Li, Qiong; Feng, Jiange; Liu, Qiang; Zhang, Zuojun; Wang, Xicheng; Zhang, Xiaoyun; Mu, Xindong; ChemSusChem; vol. 7; nb. 1; (2014); p. 105 - 109 View in Reaxys

O HO

O

B HO

O N

Rx-ID: 41237245 View in Reaxys 14/146 Yield 100 %

Conditions & References With trifluorormethanesulfonic acid, water, palladium diacetate, 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine in 1,2-dimethoxyethane, Time= 12h, T= 60 °C Yousuf, Md; Das, Tuluma; Adhikari, Susanta; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8763 - 8770 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

11/62

2018-05-06 22:32:29

O

O

O HO

O

O

B HO

O N

Rx-ID: 41237246 View in Reaxys 15/146 Yield

Conditions & References

90 %, 10 %

With trifluorormethanesulfonic acid, water, palladium diacetate, 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine in 1,4-dioxane, Time= 12h, T= 60 °C , Catalytic behavior, Solvent Yousuf, Md; Das, Tuluma; Adhikari, Susanta; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8763 - 8770 View in Reaxys

20 %, 80 %

With trifluorormethanesulfonic acid, water, palladium diacetate, 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine, Time= 12h, T= 60 °C , Catalytic behavior, Temperature Yousuf, Md; Das, Tuluma; Adhikari, Susanta; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8763 - 8770 View in Reaxys

O

O

O

O

Rx-ID: 41237274 View in Reaxys 16/146 Yield

Conditions & References With trifluorormethanesulfonic acid, water, 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine in 1,2-dimethoxyethane, T= 60 °C Yousuf, Md; Das, Tuluma; Adhikari, Susanta; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8763 - 8770 View in Reaxys

OH

O

Rx-ID: 318649 View in Reaxys 17/146 Yield

Conditions & References With potassium dichromate, sulfuric acid Davies; Dixon; Jones; Journal of the Chemical Society; (1930); p. 468,470 View in Reaxys

36 % Chromat.

Time= 168h, T= 30 °C , by Corynebacterium equi IFO 3730 Ohta, Hiromichi; Yamada, Hiroshi; Tsuchihashi, Gen-ichi; Agricultural and Biological Chemistry; vol. 49; nb. 8; (1985); p.

2459 - 2462

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

12/62

2018-05-06 22:32:29

View in Reaxys With lyophilized cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, Time= 24h, T= 24 °C , pH= 8.0 Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 402 - 406 View in Reaxys With ketoreductase, acetone in phosphate buffer, pentane, T= 24.99 °C , pH= 7.3, Equilibrium constant, Further Variations: Solvents Tewari, Yadu B.; Kishore, Nand; Rozzell, J. David; Vanderah, David J.; Schantz, Michele M.; Journal of Chemical Thermodynamics; vol. 38; nb. 10; (2006); p. 1165 - 1171 View in Reaxys 95 %Chromat.

With ammonium cerium (IV) nitrate, lithium bromide in water, acetonitrile, Time= 5h, T= 65 °C Nikishin; Sokova; Kapustina; Russian Chemical Bulletin; vol. 59; nb. 2; (2010); p. 391 - 395 View in Reaxys

92 %Spectr. 4.6 Oxidation of alcohols under open-air atmosphere General procedure: VOSO4·5H2O (126.5 mg, 0.5 mmol), 4,4η-di-tert-butyl-2,2η-bipyridyl (268.4 mg, 1 mmol), and p-nitrobenzhydrol (229.3 mg, 0.05 mmol) were placed in a 100 mL round-bottomed flask, and then water (50 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (18.06 g, 150 mmol) was slowly added into the mixture (cooling by ice water).

After that, substrate (10 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 °C for the appropriate time under open-air atmosphere. After the reaction, the mixture was extracted with ethyl acetate and dried over anhydrous MgSO4. The extracts were concentrated in vacuo. Purification of the products was carried out by silica gel column chromatography using hexane and diethyl ether as eluent to afford the analytically pure ketones. In Table 7 (entries 3, 7, and 8), crude products were purified by recrystallization with ethyl acetate in refrigerator, afforded analytically pure ketones. The product was identified by comparison with the commercially available sample using 1H NMR spectroscopy.

With magnesium sulphate, vanadyl(IV) sulphate pentahydrate, 4-nitrophenyl(phenyl)methanol, 4,4'-di-tert-butyl-2,2'- bipyridine in water, Time= 120h, T= 0 - 90 °C , p= 750.075Torr Marui, Kuniaki; Higashiura, Yuuki; Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Tetrahedron; vol. 70; nb. 14; (2014); p. 2431 - 2438 View in Reaxys 76 %Chromat.

4.3. General procedure for catalytic aerobic oxidation of primaryalcohols in water General procedure: A mixture of magnetic nanoparticles 1a-e (suspension in ethanol; 0.16 M CoePd), primary alcohol (0.2 mmol), and potassium carbonate (0.2 mmol) in water (2 mL) was stirred at 60 C under oxygen gas at atmospheric pressure.

After being cooled, the mixture was washed with ether, and acidified with 5percent hydrochloric acid. The mixture was extracted with ethyl acetate (51 mL). The extract was dried over magnesium sulfate. The resulting solution was analyzed by GC and GCMS (with Mass Spectral Reference Database). The yield of the product was determined by GC with aninternal standard (o-xylene).

With Co0.44Pd0.56, oxygen, potassium carbonate in ethanol, water, T= 60 °C , p= 760.051Torr Ito, Yoshikazu; Ohta, Hidetoshi; Yamada, Yoichi M.A.; Enoki, Toshiaki; Uozumi, Yasuhiro; Tetrahedron; nb. 36; (2014); p.

6146 - 6149 View in Reaxys

76 %Chromat.

4.4. General procedure for catalytic aerobic oxidation of secondary alcohols in water General procedure: A mixture of magnetic nanoparticles 1a (suspension in ethanol) and secondary alcohol (0.2 mmol) in water (2 mL) was stirred at 60°C under oxygen gas at atmospheric pressure. After it was cooled, the mixture was extracted with ethyl acetate (51 mL). The extract was analyzed by GC and GC-MS (with Mass Spectral Reference Database). The yield of the product was determined by GC with an internal standard (o-xylene or mesitylene).

With oxygen in water, Time= 24h, T= 60 °C , p= 760.051Torr Ito, Yoshikazu; Ohta, Hidetoshi; Yamada, Yoichi M.A.; Enoki, Toshiaki; Uozumi, Yasuhiro; Tetrahedron; vol. 70; nb. 36; (2014); p. 6146 - 6149 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

13/62

2018-05-06 22:32:29

N

O O

Rx-ID: 8768497 View in Reaxys 18/146 Yield 78 %

Conditions & References With 5-palladium/activated carbon in toluene, Time= 40h, T= 120 °C , Inert atmosphere, Heck Reaction, Temperature, Time, regioselective reaction Yoon, Il Chul; Kim, Tae Gyun; Cho, Chan Sik; Organometallics; vol. 33; nb. 7; (2014); p. 1890 - 1892 View in Reaxys

69 %

With tris(triphenylphosphine)ruthenium(II) chloride in 1,4-dioxane, Time= 40h, T= 180 °C , Product distribution, Further Variations: Reagents Cho, Chan Sik; Kim, Bok Tae; Lee, Myung Jin; Kim, Tae-Jeong; Shim, Sang Chul; Angewandte Chemie, International Edition; vol. 40; nb. 5; (2001); p. 958 - 960; Angewandte Chemie; vol. 113; (2001); p. 984 - 986 View in Reaxys

H

O

O

Rx-ID: 22146402 View in Reaxys 19/146 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: K2cr2O7; aqueous sulfuric acid With potassium dichromate, diethyl ether, sulfuric acid Davies; Dixon; Jones; Journal of the Chemical Society; (1930); p. 468,470 View in Reaxys Reaction Steps: 2 1: water / 96 h / 21 °C 2: tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere in tetrahydrofuran, water Akhbar, Ahmed R.; Chudasama, Vijay; Fitzmaurice, Richard J.; Powell, Lyn; Caddick, Stephen; Chemical Communications; vol. 50; nb. 6; (2014); p. 743 - 746 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

14/62

2018-05-06 22:32:29

O

O

O

N

O

NH

Mg Br O

O

Rx-ID: 36862419 View in Reaxys 20/146 Yield 71 %

Conditions & References in tetrahydrofuran, Time= 0.5h, T= -78 °C , Inert atmosphere Akhbar, Ahmed R.; Chudasama, Vijay; Fitzmaurice, Richard J.; Powell, Lyn; Caddick, Stephen; Chemical Communications; vol. 50; nb. 6; (2014); p. 743 - 746 View in Reaxys

N

O

O

Rx-ID: 37618811 View in Reaxys 21/146 Yield 10 %, 36 %

Conditions & References With 5-palladium/activated carbon in toluene, Time= 40h, T= 150 °C , Inert atmosphere, Heck Reaction, Temperature, Time, regioselective reaction Yoon, Il Chul; Kim, Tae Gyun; Cho, Chan Sik; Organometallics; vol. 33; nb. 7; (2014); p. 1890 - 1892 View in Reaxys O

Br Br

O

O

O

O

O

O

Rx-ID: 39056886 View in Reaxys 22/146

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

15/62

2018-05-06 22:32:29

Yield

Conditions & References Stage 1: With bis(1,5-cyclooctadiene)nickel (0), 4,4'-di-tert-butyl-2,2'- bipyridine in tetrahydrofuran-d8, Time= 0.0833333h, Inert atmosphere, Glovebox, Sealed tube Stage 2: in tetrahydrofuran-d8, N,N-dimethyl acetamide, Time= 14h, T= 60 °C , Sealed tube Wotal, Alexander C.; Ribson, Ryan D.; Weix, Daniel J.; Organometallics; vol. 33; nb. 20; (2014); p. 5874 - 5881 View in Reaxys

Br Br

O

O

O

Rx-ID: 39056887 View in Reaxys 23/146 Yield

Conditions & References Stage 1: With bis(1,5-cyclooctadiene)nickel (0), 4,4'-di-tert-butyl-2,2'- bipyridine in tetrahydrofuran-d8, Time= 0.0833333h, Inert atmosphere, Glovebox, Sealed tube Stage 2: With zinc in tetrahydrofuran-d8, N,N-dimethyl acetamide, Time= 14h, T= 60 °C , Sealed tube Wotal, Alexander C.; Ribson, Ryan D.; Weix, Daniel J.; Organometallics; vol. 33; nb. 20; (2014); p. 5874 - 5881 View in Reaxys

Cl Li

O

O

Rx-ID: 35484366 View in Reaxys 24/146 Yield 94 %Chromat.

Conditions & References Partial alkylation of acid chlorides to corresponding ketones General procedure: The following experimental procedure for the partial reduction of benzoyl chloride to 1-phenylpentanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.11 mL, 1.25 mmol) and 10 mL THF. After cooling to 0 °C, DIBALH (1.2 mL, 1.0 M in hexane, 1.2 mmol) was added dropwise and stirred for 3 h at same temperature. To the reaction mixture was slowly added benzoyl chloride (0.116 mL, 1.0 mmol) and stirred for 10 min. Then, n-BuLi (1.25 mL, 1.6 M in hexane, 2.0 mmol) was added and the mixture was stirred for 10 min again. The reaction was stopped by aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2 × 10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1-phenylpentanone (159 mg, 98percent). All products in Table 3 were confirmed by comparison with NMR data reported in the literature.8 Stage 1: With morpholine, diisobutylaluminium hydride in tetrahydrofuran, hexane, Time= 0.166667h, T= 0 °C , Inert atmosphere Stage 2: in tetrahydrofuran, hexane, Time= 0.166667h, T= 0 °C Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3199 - 3203 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

16/62

2018-05-06 22:32:29

O

O

O

HO

OH

O

Rx-ID: 35656989 View in Reaxys 25/146 Yield

Conditions & References 1 : Example 1 [0095] An oxidation reaction of cyclohexylbenzene and oxygen was conducted at a temperature of 105°C and a pressure of 0 psi, gauge (0 kPa, gauge) using 1000 ppm of N- hydroxyphthalimide as the oxidation catalyst. The oxygen source was air containing 21 wtpercent oxygen, the wtpercent based upon the weight of the air. The concentrations (millimolar) of 6- hydroperoxyhexaphenone (HP-HexPhone), 6-hydroxyhexaphenone (OH-HexPhone), and 1- phenyl-l-hexaphenone (HexPhone) were tracked over time, and compared to the concentrations of these byproducts predicted by the kinetic model: With N -hydroxyphthalimide, oxygen, T= 105 °C , p= 0Torr , Concentration, Temperature Patent; EXXONMOBIL CHEMICAL PATENTS INC.; PATEL, Bryan, A.; BENITEZ, Francisco, M.; SMITH, Charles, M.; DAKKA, Jihad, M.; REINE, Travis, A.; WO2013/95791; (2013); (A1) English View in Reaxys

OH

OH O

O

Rx-ID: 8958602 View in Reaxys 26/146 Yield 88 % Chromat., 4 % Chromat.

Conditions & References With potassium hydroxide, bis(1,5-cyclooctadiene)diiridium(I) dichloride, triphenylphosphine, Time= 4h, T= 100 °C Taguchi, Kazuhiko; Nakagawa, Hideto; Hirabayashi, Tomotaka; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of the American Chemical Society; vol. 126; nb. 1; (2004); p. 72 - 73 View in Reaxys With potassium hydroxide, Grubbs catalyst first generation in 1,4-dioxane, Time= 40h, T= 80 °C , Product distribution, Further Variations: Catalysts, Temperatures Cho; Kim; Shim; Journal of Organic Chemistry; vol. 66; nb. 26; (2001); p. 9020 - 9022 View in Reaxys

80 %Chromat., 7 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], potassium hydoxide, Time= 0.166667h, T= 110 °C , Inert atmosphere, Aldol Condensation, Reagent/catalyst, Temperature, Time Li, Jian; Zhang, Weixing; Wang, Feng; Jiang, Min; Dong, Xiaochun; Zhao, Weili; Chinese Journal of Chemistry; vol. 30; nb. 10; (2012); p. 2363 - 2366,4 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

17/62

2018-05-06 22:32:29

Cl

Br

Mg

O

O

Rx-ID: 31336777 View in Reaxys 27/146 Yield 91 %

Conditions & References Stage 1: With 1-methyl-pyrrolidin-2-one in toluene, Time= 0.5h, T= 0 °C Stage 2: in tetrahydrofuran, toluene, Time= 4.25h, T= -10 - 0 °C , chemoselective reaction Gowda, Maravanhalli Sidde; Pande, Sushanth Sudhir; Ramakrishna, Ramesha Andagar; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 9; nb. 15; (2011); p. 5365 - 5368 View in Reaxys

O S–

Na +

O

O

O

Rx-ID: 31357050 View in Reaxys 28/146 Yield 23 %

Conditions & References With chloro(1,5-cyclooctadiene)rhodium(I) dimer, oxygen in toluene, Time= 24h, T= 20 - 165 °C , p= 760.051Torr Rao, Honghua; Yang, Luo; Shuai, Qi; Li, Chao-Jun; Advanced Synthesis and Catalysis; vol. 353; nb. 10; (2011); p. 1701 1706 View in Reaxys

O

O

Rx-ID: 29646891 View in Reaxys 29/146 Yield

Conditions & References With trichlorosilane, Triphenylphosphine oxide in 1,2-dichloro-ethane, T= 0 °C , Inert atmosphere, chemoselective reaction Cao, Jun-Jie; Zhou, Feng; Zhou, Jian; Angewandte Chemie - International Edition; vol. 49; nb. 29; (2010); p. 4976 - 4980 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

18/62

2018-05-06 22:32:29

O

OH

O

Rx-ID: 29757499 View in Reaxys 30/146 Yield 84 %

Conditions & References With fluorous-organic hybrid ether, F-626, Time= 2h, T= 200 °C , Inert atmosphere Fukuyama, Takahide; Kawamoto, Takuji; Okamura, Takahiro; Denichoux, Aurelien; Ryu, Ilhyong; Synlett; nb. 14; (2010); p. 2193 - 2196; Art.No: U04110ST View in Reaxys

O

HO

O

Rx-ID: 29757505 View in Reaxys 31/146 Yield 98 %

Conditions & References With fluorous-organic hybrid ether, F-626, Time= 4h, T= 200 °C , Inert atmosphere Fukuyama, Takahide; Kawamoto, Takuji; Okamura, Takahiro; Denichoux, Aurelien; Ryu, Ilhyong; Synlett; nb. 14; (2010); p. 2193 - 2196; Art.No: U04110ST View in Reaxys

O

O

HO

O

Rx-ID: 29757506 View in Reaxys 32/146 Yield

Conditions & References With fluorous-organic hybrid ether, F-626, Time= 4h, T= 200 °C , Inert atmosphere Fukuyama, Takahide; Kawamoto, Takuji; Okamura, Takahiro; Denichoux, Aurelien; Ryu, Ilhyong; Synlett; nb. 14; (2010); p. 2193 - 2196; Art.No: U04110ST View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

19/62

2018-05-06 22:32:29

HO

HO

B HO

O

O

Rx-ID: 29902163 View in Reaxys 33/146 Yield 77 %

Conditions & References With tetrakis(triphenylphosphine) palladium(0), water, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline in N,N-dimethyl-formamide, Time= 15h, T= 60 °C , Inert atmosphere Kwon, Young Bum; Choi, Bo Ram; Lee, Seung Hwan; Seo, Jin-Soo; Yoon, Cheol Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 9; (2010); p. 2672 - 2674 View in Reaxys

OH

O

Br

O

Rx-ID: 30669245 View in Reaxys 34/146 Yield 39 %Chromat., 57 %Chromat.

Conditions & References With ammonium cerium (IV) nitrate, lithium bromide in water, acetonitrile, Time= 7h, T= 65 °C Nikishin; Sokova; Kapustina; Russian Chemical Bulletin; vol. 59; nb. 2; (2010); p. 391 - 395 View in Reaxys

O

HO

O

Rx-ID: 28386517 View in Reaxys 35/146 Yield 54 %, 38 %

Conditions & References With 2-Iodobenzoic acid, potassium hydrogen persulfate, water in acetonitrile, Time= 8h Ojha, Lawanya R.; Kudugunti, Shashi; Maddukuri, Padma P.; Kommareddy, Amitha; Gunna, Meena R.; Dokuparthi, Praveen; Gottam, Hima B.; Botha, Kiran K.; Parapati, Divya R.; Vinod, Thottumkara K.; Synlett; nb. 1; (2009); p. 117 121 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

20/62

2018-05-06 22:32:29

OH HO

O

Rx-ID: 28724635 View in Reaxys 36/146 Yield

Conditions & References

67 %

With caesium carbonate in para-xylene, Time= 48h, T= 145 °C , Inert atmosphere Shimizu, Ken-ichi; Sato, Ryosuke; Satsuma, Atsushi; Angewandte Chemie, International Edition; vol. 48; (2009); p. 3982 3986; Angewandte Chemie; vol. 121; (2009); p. 4042 - 4046 View in Reaxys

H 2N

O

O

Rx-ID: 29118595 View in Reaxys 37/146 Yield

Conditions & References Stage 1: With [(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)-bis(trifluoromethanesulfonyl)imidate]gold(I) complex in acetonitrile, Time= 24h, T= 80 °C Stage 2: With hydrogenchloride, water in acetonitrile, T= 20 °C , regioselective reaction Leyva, Antonio; Corma, Avelino; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2876 - 2886 View in Reaxys HO

O

B

O

HO

O

HO

O O

Rx-ID: 9234190 View in Reaxys 38/146 Yield 95 %

Conditions & References With P(p-CH3OC6H4)3, palladium diacetate in tetrahydrofuran, water, Time= 16h, T= 60 °C Goossen, Lukas J.; Ghosh, Keya; European Journal of Organic Chemistry; nb. 19; (2002); p. 3254 - 3267 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

21/62

2018-05-06 22:32:29

With palladium diacetate, triphenylphosphine in water, toluene, Time= 3h, T= 55 °C , Inert atmosphere, Overall yield = 80.3 percent Pink, Christopher J.; Wong, Hau-To; Ferreira, Frederico C.; Livingston, Andrew G.; Organic Process Research and Development; vol. 12; nb. 4; (2008); p. 589 - 595 View in Reaxys

O O HO

O

B HO

O

Rx-ID: 28160834 View in Reaxys 39/146 Yield 5%

Conditions & References With sodium carbonate, palladium dichloride in water, acetone, Time= 1.5h, T= 20 °C , Inert atmosphere, Suzuki type reaction Xin, Bing-Wei; Synthetic Communications; vol. 38; nb. 16; (2008); p. 2826 - 2837 View in Reaxys

HO

O

B

O

O

HO

O

Rx-ID: 8988110 View in Reaxys 40/146 Yield 88 %

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane, Time= 5h, T= 80 °C Kakino, Ryuki; Yasumi, Sayaka; Shimizu, Isao; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 75; nb. 1; (2002); p. 137 - 148 View in Reaxys

30 %

With water, sodium carbonate, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, palladium diacetate, Time= 12h, T= 60 °C , Suzuki reaction Xin, Bingwei; Zhang, Yuhong; Cheng, Kai; Journal of Organic Chemistry; vol. 71; nb. 15; (2006); p. 5725 - 5731 View in Reaxys

97 % Chromat.

With palladium diacetate, triphenylphosphine in tetrahydrofuran, Time= 16h Gossen, Lukas J.; Ghosh, K.; Angewandte Chemie, International Edition; vol. 40; nb. 18; (2001); p. 3458 - 3460; Angewandte Chemie; vol. 40; nb. 18; (2001); p. 3458 - 3468 View in Reaxys With sodium dodecyl-sulfate, potassium carbonate, palladium dichloride in water, Time= 6h, T= 60 °C Xin, Bingwei; Zhang, Yuhong; Cheng, Kai; Synthesis; nb. 13; (2007); p. 1970 - 1978 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

22/62

2018-05-06 22:32:29

O Br

O

Rx-ID: 10404680 View in Reaxys 41/146 Yield 92 %

Conditions & References With air, triethyl borane, di-n-butylchlorogermane in tetrahydrofuran, hexane, Time= 1h, T= 0 - 20 °C Miura, Katsukiyo; Ootsuka, Kazunori; Hosomi, Akira; Synlett; nb. 20; (2005); p. 3151 - 3153; Art.No: U28405ST View in Reaxys Reaction Steps: 2 1: 97 percent / NaI / acetone / 2.5 h / Heating 2: 87 percent / PhSiH3; 2,6-lutidine; air / In(OAc)3 / ethanol / 1.5 h / 20 °C With 2,6-dimethylpyridine, air, phenylsilane, sodium iodide, In(OAc)3 in ethanol, acetone Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira; Journal of Organic Chemistry; vol. 72; nb. 3; (2007); p. 787 - 792 View in Reaxys Reaction Steps: 2 1: 97 percent / NaI / acetone / 2.5 h / Heating 2: 20 percent / PhSiH3; Et3B; air / In(OAc)3 / tetrahydrofuran; hexane / 24 h / 30 °C With air, triethyl borane, phenylsilane, sodium iodide, In(OAc)3 in tetrahydrofuran, hexane, acetone Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira; Journal of Organic Chemistry; vol. 72; nb. 3; (2007); p. 787 - 792 View in Reaxys

Br

O

Rx-ID: 10505797 View in Reaxys 42/146 Yield 30 % Turnov.

Conditions & References With hydrogen bromide, dihydrogen peroxide in dichloromethane, water, Time= 30h, T= 20 °C Khan, Abu T.; Parvin, Tasneem; Choudhury, Lokman H.; Ghosh, Subrata; Tetrahedron Letters; vol. 48; nb. 13; (2007); p.

2271 - 2274 View in Reaxys O

Br

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

23/62

2018-05-06 22:32:29

OH

OH Br

O

Rx-ID: 10511992 View in Reaxys 43/146 Yield 38 %, 27 %

Conditions & References With air, triethyl borane, phenylsilane, In(OAc)3 in tetrahydrofuran, hexane, Time= 24h, T= 30 °C Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira; Journal of Organic Chemistry; vol. 72; nb. 3; (2007); p. 787 - 792 View in Reaxys

29 %, 12 %, With phenylsilane, In(OAc)3 in tetrahydrofuran, Time= 24h, T= 70 °C 32 % Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira; Journal of Organic Chemistry; vol. 72; nb. 3; (2007); p. 787 - 792 View in Reaxys

O I

O

Rx-ID: 10531300 View in Reaxys 44/146 Yield 87 %

Conditions & References With 2,6-dimethylpyridine, air, phenylsilane, In(OAc)3 in ethanol, Time= 1.5h, T= 20 °C Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira; Journal of Organic Chemistry; vol. 72; nb. 3; (2007); p. 787 - 792 View in Reaxys O

I

OH

OH

I

O

Rx-ID: 10531301 View in Reaxys 45/146 Yield 20 %, 53 %

Conditions & References With air, triethyl borane, phenylsilane, In(OAc)3 in tetrahydrofuran, hexane, Time= 24h, T= 30 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

24/62

2018-05-06 22:32:29

Miura, Katsukiyo; Tomita, Mitsuru; Yamada, Yusuke; Hosomi, Akira; Journal of Organic Chemistry; vol. 72; nb. 3; (2007); p. 787 - 792 View in Reaxys

HO

Cl

B

O

HO

O

Rx-ID: 10312045 View in Reaxys 46/146 Yield 54 %

Conditions & References With water, sodium carbonate, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, palladium diacetate, Time= 2h, T= 60 °C , Suzuki reaction Xin, Bingwei; Zhang, Yuhong; Cheng, Kai; Journal of Organic Chemistry; vol. 71; nb. 15; (2006); p. 5725 - 5731 View in Reaxys

HO B N

HO

O

Rx-ID: 10336132 View in Reaxys 47/146 Yield 72 %

Conditions & References With [Pd(.mu.-OH)(2,2'-bipyridine)]2(OSO2CF3)2 in nitromethane, Time= 24h, Heating Zhao, Baowei; Lu, Xiyan; Organic Letters; vol. 8; nb. 26; (2006); p. 5987 - 5990 View in Reaxys

38 %

With [2,2]bipyridinyl, potassium fluoride, acetic acid, palladium diacetate in tetrahydrofuran, Time= 48h, T= 80 °C Zhao, Baowei; Lu, Xiyan; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6765 - 6768 View in Reaxys

H 2N O

O

Rx-ID: 9804247 View in Reaxys 48/146 Yield

Conditions & References Stage 1: With [(dppe)Pd(H2O)2](OTf)2 in 1,4-dioxane, Time= 24h, T= 80 °C Stage 2: With silica gel in dichloromethane, Time= 2h, T= 20 °C Shimada, Tomohiro; Bajracharya, Gan B.; Yamamoto, Yoshinori; European Journal of Organic Chemistry; nb. 1; (2005); p.

59 - 62

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

25/62

2018-05-06 22:32:29

View in Reaxys

HN

O

O

Rx-ID: 9810360 View in Reaxys 49/146 Yield

Conditions & References Stage 1: With [(dppe)Pd(H2O)2](OTf)2 in 1,4-dioxane, Time= 7h, T= 80 °C Stage 2: With silica gel in dichloromethane, Time= 2h, T= 20 °C Shimada, Tomohiro; Bajracharya, Gan B.; Yamamoto, Yoshinori; European Journal of Organic Chemistry; nb. 1; (2005); p.

59 - 62 View in Reaxys O O

O O

O

O

O

O

Rx-ID: 10390660 View in Reaxys 50/146 Yield

Conditions & References

46 % Chromat.

With aluminum oxide, T= 449.85 °C , Title compound not separated from byproducts Glinski; Koscik; Jerzak; Synoradzki; Polish Journal of Chemistry; vol. 79; nb. 6; (2005); p. 995 - 1001 View in Reaxys

S

O S

Rx-ID: 4794687 View in Reaxys 51/146

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

26/62

2018-05-06 22:32:29

Yield

Conditions & References

94 %

With sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene in methanol, Time= 3h, T= 20 °C Ichige, Takahiro; Miyake, Annu; Kanoh, Naoki; Nakata, Masaya; Synlett; nb. 10; (2004); p. 1686 - 1690 View in Reaxys

77 % Chromat.

With 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one in water, acetonitrile, Time= 3h, Ambient temperature Ochiai, Masahito; Nakanishi, Akinobu; Ito, Takao; Journal of Organic Chemistry; vol. 62; nb. 13; (1997); p. 4253 - 4259 View in Reaxys

O

I

O

O

Rx-ID: 9303349 View in Reaxys 52/146 Yield

Conditions & References

19 %, 81 %

With 2,4,6-trimethyl-pyridine, 2,2'-azobis(isobutyronitrile) in benzene, Time= 3h, Heating Cai, Yudong; Roberts, Brian P.; Tetrahedron Letters; vol. 44; nb. 25; (2003); p. 4645 - 4648 View in Reaxys With 2,3,5-trimethyl-pyridine, 2,2'-azobis(isobutyronitrile) in benzene, Time= 3h, Heating, Title compound not separated from byproducts Cai, Yudong; Roberts, Brian P.; Tocher, Derek A.; Barnett, Sarah A.; Organic and Biomolecular Chemistry; vol. 2; nb. 17; (2004); p. 2517 - 2529 View in Reaxys

N

O

HO B

O HO

O

Rx-ID: 9686192 View in Reaxys 53/146 Yield 75 %

Conditions & References With palladium diacetate, triphenylphosphine in 1,4-dioxane, Time= 10h, T= 50 °C Tatamidani, Hiroto; Kakiuchi, Fumitoshi; Chatani, Naoto; Organic Letters; vol. 6; nb. 20; (2004); p. 3597 - 3599 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

27/62

2018-05-06 22:32:29

O

O

I

O

Rx-ID: 9772005 View in Reaxys 54/146 Yield 83 %

Conditions & References With 2,2,6,6-tetramethyl-piperidine, di-tert-amyl peroxide in octane, Time= 4h, Heating Cai, Yudong; Roberts, Brian P.; Tocher, Derek A.; Barnett, Sarah A.; Organic and Biomolecular Chemistry; vol. 2; nb. 17; (2004); p. 2517 - 2529 View in Reaxys

O

N O

O

Rx-ID: 9876260 View in Reaxys 55/146 Yield 100 %

Conditions & References With sodium nitrite in water, dimethyl sulfoxide, Time= 148h, T= 20 °C Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys Reaction Steps: 2 1: 35 percent / sodium nitrite / dimethylsulfoxide; H2O / 72 h / 71 °C 2: 40 percent / NOBF4 / dimethylsulfoxide / 0.08 h With nitrosonium tetrafluoroborate, sodium nitrite in water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys

HO N

O

N O

O

Rx-ID: 9876261 View in Reaxys 56/146 Yield 65 %, 35 %

Conditions & References With sodium nitrite in water, dimethyl sulfoxide, Time= 72h, T= 71 °C Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

28/62

2018-05-06 22:32:29

View in Reaxys

HO N

O

Rx-ID: 9878842 View in Reaxys 57/146 Yield

Conditions & References

40 %

With nitrosonium tetrafluoroborate in dimethyl sulfoxide, Time= 0.0833333h Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys

O N O

O B

O

O

Rx-ID: 10026344 View in Reaxys 58/146 Yield 72 %

Conditions & References With dodecacarbonyl-triangulo-triruthenium in toluene, Time= 20h, T= 140 °C Tatamidani, Hiroto; Yokota, Kazuhiko; Kakiuchi, Fumitoshi; Chatani, Naoto; Journal of Organic Chemistry; vol. 69; nb.

17; (2004); p. 5615 - 5621 View in Reaxys

O N O

3,4-dichloro-benzaldehyde butylimine O

Rx-ID: 13127248 View in Reaxys 59/146 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h 2.1: 100 percent / sodium nitrite / dimethylsulfoxide; H2O / 148 h / 20 °C With n-butyllithium, sodium nitrite in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

29/62

2018-05-06 22:32:29

Reaction Steps: 3 1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h 2.1: 35 percent / sodium nitrite / dimethylsulfoxide; H2O / 72 h / 71 °C 3.1: 40 percent / NOBF4 / dimethylsulfoxide / 0.08 h With n-butyllithium, nitrosonium tetrafluoroborate, sodium nitrite in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h 2.1: 65 percent / sodium nitrite / dimethylsulfoxide; H2O / 72 h / 71 °C With n-butyllithium, sodium nitrite in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys

Br

O

Rx-ID: 13129707 View in Reaxys 60/146 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h 2.1: 100 percent / sodium nitrite / dimethylsulfoxide; H2O / 148 h / 20 °C With n-butyllithium, sodium nitrite in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys Reaction Steps: 3 1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h 2.1: 35 percent / sodium nitrite / dimethylsulfoxide; H2O / 72 h / 71 °C 3.1: 40 percent / NOBF4 / dimethylsulfoxide / 0.08 h With n-butyllithium, nitrosonium tetrafluoroborate, sodium nitrite in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h 2.1: 65 percent / sodium nitrite / dimethylsulfoxide; H2O / 72 h / 71 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

30/62

2018-05-06 22:32:29

With n-butyllithium, sodium nitrite in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, hexane, water, dimethyl sulfoxide Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys Reaction Steps: 4 1: diluted alcohol 2: alcoholic NaOH-solution 3: phosphorus trichloride / 110 - 120 °C 4: aluminium chloride With sodium hydroxide, aluminium trichloride, ethanol, phosphorus trichloride Simon; Bulletin des Societes Chimiques Belges; vol. 38; (1929); p. 50; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2520 View in Reaxys

[Rh(PEt3)2(μ-NH(p-tolyl))]2 O

Rx-ID: 13165945 View in Reaxys 61/146 Yield

Conditions & References Reaction Steps: 2 1.1: iodine; mercuric oxide / diethyl ether / 3 h / 20 °C 1.2: 76 percent / t-BuOK / diethyl ether; tetrahydrofuran / 20 °C 2.1: AIBN; collidine / benzene / 3 h / Heating With 2,3,5-trimethyl-pyridine, 2,2'-azobis(isobutyronitrile), iodine, mercury(II) oxide in diethyl ether, benzene Cai, Yudong; Roberts, Brian P.; Tocher, Derek A.; Barnett, Sarah A.; Organic and Biomolecular Chemistry; vol. 2; nb. 17; (2004); p. 2517 - 2529 View in Reaxys Reaction Steps: 2 1.1: iodine; mercuric oxide / diethyl ether / 3 h / 20 °C 1.2: t-BuOK / diethyl ether; tetrahydrofuran / 20 °C 2.1: 83 percent / 2,2,6,6-tetramethylpiperidine; di-tert-amyl peroxide / octane / 4 h / Heating With 2,2,6,6-tetramethyl-piperidine, di-tert-amyl peroxide, iodine, mercury(II) oxide in octane, diethyl ether Cai, Yudong; Roberts, Brian P.; Tocher, Derek A.; Barnett, Sarah A.; Organic and Biomolecular Chemistry; vol. 2; nb. 17; (2004); p. 2517 - 2529 View in Reaxys

Cl

O

O

Rx-ID: 13524611 View in Reaxys 62/146 Yield

Conditions & References Reaction Steps: 2

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

31/62

2018-05-06 22:32:29

1: 75 percent / Pd(OAc)2; PPh3 / dioxane / 10 h / 50 °C With palladium diacetate, triphenylphosphine in 1,4-dioxane Tatamidani, Hiroto; Kakiuchi, Fumitoshi; Chatani, Naoto; Organic Letters; vol. 6; nb. 20; (2004); p. 3597 - 3599 View in Reaxys

H

O

O

Rx-ID: 4625575 View in Reaxys 63/146 Yield 83 %

Conditions & References With 3-methylpyridin-2-ylamine, aniline, benzoic acid, Wilkinson's catalyst in toluene, Time= 1h, T= 130 °C Jun, Chul-Ho; Lee, Dae-Yon; Lee, Hyuk; Hong, Jun-Bae; Angewandte Chemie (International Edition in English); vol. 39; nb.

17; (2000); p. X3070-3072 View in Reaxys

75 %

With 3-methylpyridin-2-ylamine, Wilkinson's catalyst in toluene, Time= 24h, T= 150 °C Jun, Chul-Ho; Lee, Hyuk; Hong, Jun-Bae; Journal of Organic Chemistry; vol. 62; nb. 5; (1997); p. 1200 - 1201 View in Reaxys

72 %

With 3-methylpyridin-2-ylamine, Wilkinson's catalyst in tetrahydrofuran, Time= 40h, T= 100 °C , other reagent; catalytic activities of transition metal complexes, Product distribution Jun, Chul-Ho; Lee, Hyuk; Hong, Jun-Bae; Journal of Organic Chemistry; vol. 62; nb. 5; (1997); p. 1200 - 1201 View in Reaxys

90 % Turnov.

Stage 1: With RhCl(PPh3)3, Montmorillonite K10 in toluene, Time= 2h, T= 110 °C Stage 2: With hydrogenchloride Yanez, Xiomara; Claver, Carmen; Castillon, Sergio; Fernandez, Elena; Tetrahedron Letters; vol. 44; nb. 8; (2003); p. 1631 1634 View in Reaxys

O

O I

O

Rx-ID: 9303355 View in Reaxys 64/146 Yield 85 %, 15 %

Conditions & References With 2,2,6,6-tetramethyl-piperidine, di-tert-amyl peroxide in octane, Heating Cai, Yudong; Roberts, Brian P.; Tetrahedron Letters; vol. 44; nb. 25; (2003); p. 4645 - 4648 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

32/62

2018-05-06 22:32:29

OH

OH

OH

O

Rx-ID: 9392736 View in Reaxys 65/146 Yield

Conditions & References With sodium isopropylate, acetone, [RuCl2(PPh3)(ferrocenyloxazolinylphosphine)] in isopropyl alcohol, Time= 0.666667h, T= 50 °C Nishibayashi, Yoshiaki; Yamauchi, Akiyoshi; Onodera, Gen; Uemura, Sakae; Journal of Organic Chemistry; vol. 68; nb. 15; (2003); p. 5875 - 5880 View in Reaxys

O HO

OH

O

Rx-ID: 9006796 View in Reaxys 66/146 Yield 65 % Spectr., 35 % Spectr.

Conditions & References With bis(cyclopentadienyl)titanium (III) chloride, deuteromethanol in tetrahydrofuran, T= -25 - 20 °C Moisan, Lionel; Hardouin, Christophe; Rousseau, Bernard; Doris, Eric; Tetrahedron Letters; vol. 43; nb. 11; (2002); p.

2013 - 2015 View in Reaxys

N

O O

Rx-ID: 8768503 View in Reaxys 67/146 Yield 35 %

Conditions & References With ruthenium trichloride, triphenylphosphine in 1,4-dioxane, Time= 40h, T= 180 °C Cho, Chan Sik; Kim, Bok Tae; Lee, Myung Jin; Kim, Tae-Jeong; Shim, Sang Chul; Angewandte Chemie, International Edition; vol. 40; nb. 5; (2001); p. 958 - 960; Angewandte Chemie; vol. 113; (2001); p. 984 - 986 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

33/62

2018-05-06 22:32:29

O

N H

O

O

Rx-ID: 8768508 View in Reaxys 68/146 Yield 11 %, 38 %

Conditions & References With ruthenium trichloride, triphenylphosphine in 1,4-dioxane, Time= 40h, T= 180 °C Cho, Chan Sik; Kim, Bok Tae; Lee, Myung Jin; Kim, Tae-Jeong; Shim, Sang Chul; Angewandte Chemie, International Edition; vol. 40; nb. 5; (2001); p. 958 - 960; Angewandte Chemie; vol. 113; (2001); p. 984 - 986 View in Reaxys

O

N

O

O

Rx-ID: 8768524 View in Reaxys 69/146 Yield 6 %, 80 %

Conditions & References With ruthenium trichloride, triphenylphosphine in 1,4-dioxane, Time= 40h, T= 180 °C Cho, Chan Sik; Kim, Bok Tae; Lee, Myung Jin; Kim, Tae-Jeong; Shim, Sang Chul; Angewandte Chemie, International Edition; vol. 40; nb. 5; (2001); p. 958 - 960; Angewandte Chemie; vol. 113; (2001); p. 984 - 986 View in Reaxys

O

H 2N

O

Rx-ID: 8772813 View in Reaxys 70/146 Yield 12 %, 80 %

Conditions & References With 3-methylpyridin-2-ylamine, Wilkinson's catalyst in toluene, Time= 24h, T= 170 °C Jun, Chul-Ho; Chung, Kwan-Yong; Hong, Jun-Bae; Organic Letters; vol. 3; nb. 5; (2001); p. 785 - 787 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

34/62

2018-05-06 22:32:29

Cl

Cl B

Cl

O

O

Rx-ID: 8675505 View in Reaxys 71/146 Yield

Conditions & References

76 %

Stage 1: With potassium fluoride on basic alumina, N-benzyl-N,N,N-triethylammonium chloride, zinc(II) chloride in acetonitrile, Time= 24h, T= 20 °C , insertion Stage 2: With sodium hydroxide, dihydrogen peroxide in acetonitrile, Time= 2h, T= 40 °C , Oxidation Guo, Feng; Huang, Shiwen; Shan, Zixing; Zhao, Dejie; Journal of Chemical Research - Part S; nb. 6; (2000); p. 280 - 281 View in Reaxys

N

Li

O O

O

Rx-ID: 5105114 View in Reaxys 72/146 Yield

Conditions & References in tetrahydrofuran, Time= 0.5h, T= 0 - 20 °C , Yield given Lee, Na Ra; Lee, Jae In; Synthetic Communications; vol. 29; nb. 8; (1999); p. 1249 - 1255 View in Reaxys

O

O

Rx-ID: 5224981 View in Reaxys 73/146 Yield

Conditions & References

74 %

With chromium(VI) oxide, tert.-butylhydroperoxide in dichloromethane, Time= 12h, T= 20 °C , Oxidation Chandrasekhar; Mohanty, Pradyumna K.; Ramachander; Synlett; nb. 7; (1999); p. 1063 - 1064 View in Reaxys -1

F (v4)

F

B FF

Cl N I+

O

O

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

35/62

2018-05-06 22:32:29

O OH N O

O

Rx-ID: 5279166 View in Reaxys 74/146 Yield 4 %, 8 %, 9 %, 23 %

Conditions & References With chromium dichloride, nickel dichloride in N,N-dimethyl-formamide, Time= 5h, T= 25 °C , Arylation, Product distribution Chen, Da-Wei; Ochiai, Masahito; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6804 - 6814 View in Reaxys

HO

O

Rx-ID: 4853776 View in Reaxys 75/146 Yield 91 %

Conditions & References With 2-Amino-4-methylpyridine, rhodium(III) chloride, triphenylphosphine, Time= 40h, T= 130 °C Jun, Chul-Ho; Huh, Chan-Woo; Na, Sang-Jin; Angewandte Chemie - International Edition; vol. 37; nb. 1-2; (1998); p. 145 147 View in Reaxys

O

I

O

O

Rx-ID: 4690073 View in Reaxys 76/146 Yield

Conditions & References With potassium hydroxide, Aliquat 336, Time= 20h, Ambient temperature Diez-Barra, Enrique; De la Hoz, Antonio; Loupy, Andre; Martinez-Gonzalez, Alfonso; Martinez-Merino, Victor; Merino, Sonia; Paugam, Renee; Sanchez-Verdu, Prado; Sansoulet, Jean; Torres, Jose; Tetrahedron; vol. 53; nb. 10; (1997); p.

3659 - 3668 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

36/62

2018-05-06 22:32:29

O

O

O

O

Rx-ID: 4756386 View in Reaxys 77/146 Yield

Conditions & References

79 %

With HZSM-5, Time= 12h, T= 250 °C , other catalyst: HY-Zeolite Sreekumar; Padmakumar, Raghavakaimal; Synthetic Communications; vol. 27; nb. 5; (1997); p. 777 - 780 View in Reaxys

O

(v2)

Zn

HO

O

Rx-ID: 4990254 View in Reaxys 78/146 Yield 11 %, 65 %

Conditions & References With bis(acetylacetonate)nickel(II), methyllithium in tetrahydrofuran, T= 0 °C Ichiyanagi, Tsuyoshi; Kuniyama, Satoru; Shimizu, Makoto; Fujisawa, Tamotsu; Chemistry Letters; nb. 11; (1997); p. 1149 - 1150 View in Reaxys

Sb

Cl

O

O

Rx-ID: 4434010 View in Reaxys 79/146 Yield 50 % Chromat.

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in acetonitrile, Time= 24h, T= 80 °C Fujiwara, Masahiro; Tanaka, Mutsuo; Baba, Akio; Ando, Hisanori; Souma, Yoshie; Journal of Organometallic Chemistry; vol. 508; nb. 1-2; (1996); p. 49 - 52 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

37/62

2018-05-06 22:32:29

Cl

LiSbPh6 O

O

Rx-ID: 7160574 View in Reaxys 80/146 Yield 18 % Chromat., 28 % Chromat.

Conditions & References in acetonitrile, Time= 24h, T= 80 °C Fujiwara, Masahiro; Tanaka, Mutsuo; Baba, Akio; Ando, Hisanori; Souma, Yoshie; Journal of Organometallic Chemistry; vol. 508; nb. 1-2; (1996); p. 49 - 52 View in Reaxys

O

O

O

Rx-ID: 3679020 View in Reaxys 81/146 Yield 75 %

Conditions & References With hydrogenchloride in methanol, Time= 48h, Ambient temperature Casson, Sharon; Kocienski, Philip; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1994); p. 1187 - 1192 View in Reaxys

I

m-toluic acid phenyl ester O

Rx-ID: 18469530 View in Reaxys 82/146 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / <Pd2(dba)3> / dimethylformamide / 6 h 2: 75 percent / HCl / methanol / 48 h / Ambient temperature With hydrogenchloride, tris-(dibenzylideneacetone)dipalladium(0) in methanol, N,N-dimethyl-formamide Casson, Sharon; Kocienski, Philip; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1994); p. 1187 - 1192 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

38/62

2018-05-06 22:32:29

Sn

O

O

O

Rx-ID: 18486798 View in Reaxys 83/146 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / <Pd2(dba)3> / dimethylformamide / 6 h 2: 75 percent / HCl / methanol / 48 h / Ambient temperature With hydrogenchloride, tris-(dibenzylideneacetone)dipalladium(0) in methanol, N,N-dimethyl-formamide Casson, Sharon; Kocienski, Philip; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1994); p. 1187 - 1192 View in Reaxys

I

O O

O

O

O

Rx-ID: 3382422 View in Reaxys 84/146 Yield

Conditions & References

36 % Chromat., 15 % Chromat., 4 % Chromat., 2 % Chromat.

With tetrabutylammomium bromide, Time= 20h, Ambient temperature, selective butylation of acetophenone; other phase transfer catalysts and alkylating agents, var. time and temperature conditions; also with KOTBu, Product distribution

42 % Chromat., 17 % Chromat., 3 % Chromat., 2 % Chromat.

Time= 0.0833333h, T= 80 °C

7 % Chromat., 71 % Chromat., 1 % Chro-

Time= 1h, T= 80 °C

Diaz-Ortiz; Diez-Barra; De la Hoz; Moreno; Sanchez-Verdu; Loupy; Synthetic Communications; vol. 23; nb. 7; (1993); p.

875 - 883 View in Reaxys

Diaz-Ortiz; Diez-Barra; De la Hoz; Moreno; Sanchez-Verdu; Loupy; Synthetic Communications; vol. 23; nb. 7; (1993); p.

875 - 883 View in Reaxys

Diaz-Ortiz; Diez-Barra; De la Hoz; Moreno; Sanchez-Verdu; Loupy; Synthetic Communications; vol. 23; nb. 7; (1993); p.

875 - 883 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

39/62

2018-05-06 22:32:29

mat., 3 % Chromat.

Si

tetramethylammonium pentacarbonyl(1-oxidopentylidene)chromium(0)

O

O

Rx-ID: 7160573 View in Reaxys 85/146 Yield

Conditions & References

68 %

With tris(pyridine-2-carboxylato)manganese(III) in N,N-dimethyl-formamide, Time= 1h, T= 0 °C Narasaka, Koichi; Sakurai, Hidehiro; Chemistry Letters; nb. 7; (1993); p. 1269 - 1272 View in Reaxys

Si

I

O

O

Rx-ID: 1744233 View in Reaxys 86/146 Yield

Conditions & References

27 %

With silver trifluoroacetate in dichloromethane, Time= 0.166667h, T= 25 °C Jefford, Charles W.; Sledeski, Adam W.; Lelandais, Patrick; Boukouvalas, John; Tetrahedron Letters; vol. 33; nb. 14; (1992); p. 1855 - 1858 View in Reaxys

O

O HO

O

O O

Rx-ID: 1970557 View in Reaxys 87/146 Yield 13 %, 15 %

Conditions & References With acetic anhydride, cobalt(II) chloride in acetonitrile, Time= 12h, T= 80 °C Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007 View in Reaxys O

O

O

Br

Br

Li

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

40/62

2018-05-06 22:32:29

O

O

Br

O

Rx-ID: 3912433 View in Reaxys 88/146 Yield

Conditions & References Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Kowalski, Conrad J.; Reddy, Rajarathnam E.; Journal of Organic Chemistry; vol. 57; nb. 28; (1992); p. 7194 - 7208 View in Reaxys Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given Kowalski, Conrad J.; Reddy, Rajarathnam E.; Journal of Organic Chemistry; vol. 57; nb. 28; (1992); p. 7194 - 7208 View in Reaxys O

O

Br

O

Br

O

O

Br

O

Rx-ID: 3912584 View in Reaxys 89/146 Yield

Conditions & References Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given Kowalski, Conrad J.; Reddy, Rajarathnam E.; Journal of Organic Chemistry; vol. 57; nb. 28; (1992); p. 7194 - 7208 View in Reaxys

HO

O

Rx-ID: 1970553 View in Reaxys 90/146 Yield

Conditions & References With Cumene hydroperoxide in o-xylene, Time= 35h, T= 120 °C , Yield given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

41/62

2018-05-06 22:32:29

View in Reaxys

HO

HO

O

Rx-ID: 2015426 View in Reaxys 91/146 Yield

Conditions & References With Cumene hydroperoxide, Time= 15h, T= 120 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

O

Br Mg Br

O

Rx-ID: 3403243 View in Reaxys 92/146 Yield

Conditions & References Multistep reaction Katritzky, Alan R.; Wrobel, Leszek; Savage, G. Paul; Deyrup-Drewniak, Malgorzata; Australian Journal of Chemistry; vol.

43; nb. 1; (1990); p. 133 - 139 View in Reaxys

O

Rx-ID: 21796709 View in Reaxys 93/146 Yield

Conditions & References Reaction Steps: 2 1: cumene hydroperoxide / 15 h / 120 °C 2: cumene hydroperoxide / o-xylene / 35 h / 120 °C With Cumene hydroperoxide in o-xylene Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

42/62

2018-05-06 22:32:29

View in Reaxys

Si

Li

O

Rx-ID: 1673706 View in Reaxys 94/146 Yield

Conditions & References Yield given. Multistep reaction Knochel, Paul; Xiao, Chaodong; Yeh, Ming Chang P.; Tetrahedron Letters; vol. 29; nb. 51; (1988); p. 6697 - 6700 View in Reaxys

O

Br–

N

+Mg

O

Rx-ID: 2527560 View in Reaxys 95/146 Yield 37 %

Conditions & References in tetrahydrofuran, diethyl ether, Time= 1h, T= 65 °C Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys

S

Br–

+Mg

O

O

Rx-ID: 2203015 View in Reaxys 96/146 Yield 80 % Chromat.

Conditions & References With iron(III)-acetylacetonate in tetrahydrofuran, T= 0 °C Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 26; nb. 30; (1985); p. 3595 - 3598 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

43/62

2018-05-06 22:32:29

Mg Br

O

Rx-ID: 21445103 View in Reaxys 97/146 Yield

Conditions & References Reaction Steps: 2 1: 79 percent / dichloro<1,2-bis(diphenylphosphino)ethane>nickel(II) / tetrahydrofuran / Ambient temperature 2: 80 percent Chromat. / tris(acetylacetonate)iron(III) / tetrahydrofuran / 0 °C With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride, iron(III)-acetylacetonate in tetrahydrofuran Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 26; nb. 30; (1985); p. 3595 - 3598 View in Reaxys Reaction Steps: 2 1: diethyl ether 2: K2cr2O7; aqueous sulfuric acid With potassium dichromate, diethyl ether, sulfuric acid Davies; Dixon; Jones; Journal of the Chemical Society; (1930); p. 468,470 View in Reaxys

O O

O

HO

O

O

O O

Rx-ID: 2170188 View in Reaxys 98/146 Yield

Conditions & References

2.5 % Chro- With sodium methylate in methanol, Time= 1h, electrolysis (variation of time, Pt- or C-anode), Mechanism, Product distribution mat., 0.9 % Rabjohn, Norman; Cranor, W. L.; Schofield, C. M.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1732 - 1736 Chromat., View in Reaxys 62.0 % Chromat., 3.1 % Chromat., 31.6 % Chromat.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

44/62

2018-05-06 22:32:29

O O

O

HO

O

O

O O

Rx-ID: 2170189 View in Reaxys 99/146 Yield

Conditions & References

2.5 % Chro- With sodium methylate in methanol, Time= 1h, electrolysis, Further byproducts given mat., 62.0 Rabjohn, Norman; Cranor, W. L.; Schofield, C. M.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1732 - 1736 % Chromat., 3.1 % View in Reaxys Chromat., 31.6 % Chromat.

Si

I

O

O

Rx-ID: 2856168 View in Reaxys 100/146 Yield

Conditions & References

68 %

With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium in hexane, T= -5 °C Trimitsis, G.; Beers, S.; Ridella, J.; Carlon, M.; Cullin, D.; et al.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1984); p. 1088 - 1089 View in Reaxys

O

Zn(CN)2 O

Rx-ID: 18531176 View in Reaxys 101/146 Yield

Conditions & References Reaction Steps: 2

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

45/62

2018-05-06 22:32:29

1: KH, NEt3 / tetrahydrofuran 2: 68 percent / tBuLi, TMEDA / hexane / -5 °C With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium, potassium hydride, triethylamine in tetrahydrofuran, hexane Trimitsis, G.; Beers, S.; Ridella, J.; Carlon, M.; Cullin, D.; et al.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1984); p. 1088 - 1089 View in Reaxys

O Li+

Br–

+Mg

O–

O

Rx-ID: 2436716 View in Reaxys 102/146 Yield

Conditions & References

66 %

With Grignard reagent, N,N-diphenyl-p-methoxyphenylchloromethyleniminium chloride, copper(l) iodide in tetrahydrofuran, dichloromethane, 1) -30 deg C, 1 h, 2) 0 deg C, 1 h Fujisawa, Tamotsu; Mori, Toshiki; Sato, Toshio; Tetrahedron Letters; vol. 23; nb. 48; (1982); p. 5059 - 5062 View in Reaxys With dichlorotriphenylphosphorane, 1.) CH2Cl2, THF, -30 deg C, 1 h; 2.) THF, 1 h, Yield given. Multistep reaction Fujisawa, Tamotsu; Iida, Sachio; Uehara, Hiroshi; Sato, Toshio; Chemistry Letters; (1983); p. 1267 - 1270 View in Reaxys

Br B

O

Rx-ID: 3131065 View in Reaxys 103/146 Yield

Conditions & References

26 %

With sodium hydroxide, sodium dihydrogenphosphate, dihydrogen peroxide in pentane, Time= 2h, T= 0 °C Binnewirtz, Ralf-Juergen; Klingenberger, Helmut; Welte, Rainer; Paetzold, Peter; Chemische Berichte; vol. 116; nb. 4; (1983); p. 1271 - 1284 View in Reaxys

Cl B

Si

O

Rx-ID: 3141640 View in Reaxys 104/146

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

46/62

2018-05-06 22:32:29

Yield

Conditions & References

35 %

With sodium hydroxide, sodium dihydrogenphosphate, dihydrogen peroxide in pentane, Time= 2h, T= 0 °C Binnewirtz, Ralf-Juergen; Klingenberger, Helmut; Welte, Rainer; Paetzold, Peter; Chemische Berichte; vol. 116; nb. 4; (1983); p. 1271 - 1284 View in Reaxys

Br B

Si

O

Rx-ID: 3141641 View in Reaxys 105/146 Yield

Conditions & References

34 %

With sodium hydroxide, sodium dihydrogenphosphate, dihydrogen peroxide in pentane, Time= 2h, T= 0 °C Binnewirtz, Ralf-Juergen; Klingenberger, Helmut; Welte, Rainer; Paetzold, Peter; Chemische Berichte; vol. 116; nb. 4; (1983); p. 1271 - 1284 View in Reaxys

Cl O

B

O

Rx-ID: 3529129 View in Reaxys 106/146 Yield

Conditions & References With sodium hydroxide, sodium dihydrogenphosphate, dihydrogen peroxide, 1.) 130 deg C, 1.5 h, 2.) 0 deg C, 2 h, pentane, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Binnewirtz, Ralf-Juergen; Klingenberger, Helmut; Welte, Rainer; Paetzold, Peter; Chemische Berichte; vol. 116; nb. 4; (1983); p. 1271 - 1284 View in Reaxys O

Mg Br

HO

OH

OH

O

Rx-ID: 3551820 View in Reaxys 107/146

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

47/62

2018-05-06 22:32:29

Yield

Conditions & References With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given.

Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

HO

Br–

+Mg

O O

Rx-ID: 3790103 View in Reaxys 108/146 Yield

Conditions & References With 1-chloro-1-(dimethylamino)-2-methyl-1-propene, copper(l) iodide, 1.) THF, dichloromethane, 0 deg C, 3 h; 2.) 0 deg C, 1 h, Yield given. Multistep reaction Fujisawa, Tamotsu; Mori, Toshiki; Higuchi, Kazunobu; Sato, Toshio; Chemistry Letters; (1983); p. 1791 - 1794 View in Reaxys

HO

phenylmagnesium halide O

OH

O OH

Rx-ID: 7432695 View in Reaxys 109/146 Yield

Conditions & References With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride in tetrahydrofuran, Time= 72h, Ambient temperature, Yield given.

Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride in tetrahydrofuran, Time= 72h, Ambient temperature, Yield given.

Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

HO

Phenylmagnesium halide O

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

48/62

2018-05-06 22:32:29

OH

O OH

Rx-ID: 10600631 View in Reaxys 110/146 Yield

Conditions & References in tetrahydrofuran, Time= 72h, Ambient temperature, Yield given. Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

O

N

Rx-ID: 2132134 View in Reaxys 111/146 Yield

Conditions & References With hydrogenchloride, Yield given Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys

N

O

Rx-ID: 19970057 View in Reaxys 112/146 Yield

Conditions & References Reaction Steps: 3 1: 1.) Br2 2.) n-butyllithium / 1.) THF, ; 2.) ether, -70 deg C, 30 min 2: tetrahydrofuran / 0.5 h / -65 °C 3: 1.2 N HCl With hydrogenchloride, n-butyllithium, bromine in tetrahydrofuran Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys Reaction Steps: 4 1: 1.) Br2 2.) triethylamine / 1.) ether, -60 deg C, 0.5 h then 0 deg C; 2.) ether, -20 deg C 2: 100 percent / n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -70 °C 3: tetrahydrofuran / 0.5 h / -65 °C 4: 1.2 N HCl With hydrogenchloride, n-butyllithium, bromine, triethylamine in tetrahydrofuran, diethyl ether

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

49/62

2018-05-06 22:32:29

Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys

Li

N O

Rx-ID: 19978134 View in Reaxys 113/146 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0.5 h / -65 °C 2: 1.2 N HCl With hydrogenchloride in tetrahydrofuran Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys

Br

N O

Rx-ID: 19978136 View in Reaxys 114/146 Yield

Conditions & References Reaction Steps: 3 1: 100 percent / n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -70 °C 2: tetrahydrofuran / 0.5 h / -65 °C 3: 1.2 N HCl With hydrogenchloride, n-butyllithium in tetrahydrofuran, diethyl ether Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys

N Li

O

Rx-ID: 19979540 View in Reaxys 115/146 Yield

Conditions & References Reaction Steps: 2 1: H2O / 0.17 h / -70 °C 2: 1.2 N HCl With hydrogenchloride, water

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

50/62

2018-05-06 22:32:29

Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys O Br

Br

O

Mg

Mg

O–

Br–

Br–

Mg2+

Mg2+

O–

O

Rx-ID: 2018010 View in Reaxys 116/146 Yield

Conditions & References

4 % Spectr., in tetrahydrofuran, Ambient temperature, Title compound not separated from byproducts 74 % Canonne, Persephone; Belanger, Denis; Lemay, Gilles; Tetrahedron Letters; vol. 22; nb. 50; (1981); p. 4995 - 4998 Spectr., 22 View in Reaxys % Spectr.

N N N

Li

O O

Rx-ID: 1673554 View in Reaxys 117/146 Yield

Conditions & References

20 %

in hexane, Ambient temperature, Yields of byproduct given Hassner, Alfred; Belinka, Benjamin A.; Journal of the American Chemical Society; vol. 102; nb. 19; (1980); p. 6185 - 6188 View in Reaxys

HO

O

OH

OH

O

Rx-ID: 2015427 View in Reaxys 118/146

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

51/62

2018-05-06 22:32:29

Yield 61.8 %, 5.1 %, 16.7 %, 2.1 %, 5.1 %, 3.9 %

Conditions & References With oxygen, 2,2'-azobis(isobutyronitrile), Time= 12h, T= 120 °C , various temperatures: 130 deg. C, 140 deg. C various conc. of catalyst, Product distribution, Thermodynamic data, Mechanism Velyutin, L. P.; Potekhin, V. M.; Ovchinnikov, V. I.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb. 4; (1980); p. 654 - 659; Zhurnal Organicheskoi Khimii; vol. 16; nb. 4; (1980); p. 745 - 751 View in Reaxys

O

O S

Cl

O

Rx-ID: 3584597 View in Reaxys 119/146 Yield 88 %

Conditions & References With silver perchlorate, trifluoroacetic acid in water, Time= 1h, Heating Kotake, Hiroshi; Inomata, Katsuhiko; Kinoshita, Hideki; Sakamoto, Yasuko; Kaneto, Yoko; Bulletin of the Chemical Society of Japan; vol. 53; nb. 10; (1980); p. 3027 - 3028 View in Reaxys

Fe(CO)5

I

O

Rx-ID: 19025141 View in Reaxys 120/146 Yield

Conditions & References Reaction Steps: 3 1: 1.) BuLi / 1.) THF, a.) -78 deg C, 20 min, b.) RT, 20 min, 2.) THF, from -78 deg C to RT 2: 1.) BuLi, 2.) CCl4 / 1.) THF, -78 deg C, 2.) THF, 20 min 3: 88 percent / AgClO4, CF3COOH / H2O / 1 h / Heating With tetrachloromethane, n-butyllithium, silver perchlorate, trifluoroacetic acid in water Kotake, Hiroshi; Inomata, Katsuhiko; Kinoshita, Hideki; Sakamoto, Yasuko; Kaneto, Yoko; Bulletin of the Chemical Society of Japan; vol. 53; nb. 10; (1980); p. 3027 - 3028 View in Reaxys

O

O S

O

Rx-ID: 19027778 View in Reaxys 121/146 Yield

Conditions & References Reaction Steps: 3

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

52/62

2018-05-06 22:32:29

1: 1.) BuLi / 1.) THF, a.) -78 deg C, 20 min, b.) RT, 20 min, 2.) THF, from -78 deg C to RT 2: 1.) BuLi, 2.) CCl4 / 1.) THF, -78 deg C, 2.) THF, 20 min 3: 88 percent / AgClO4, CF3COOH / H2O / 1 h / Heating With tetrachloromethane, n-butyllithium, silver perchlorate, trifluoroacetic acid in water Kotake, Hiroshi; Inomata, Katsuhiko; Kinoshita, Hideki; Sakamoto, Yasuko; Kaneto, Yoko; Bulletin of the Chemical Society of Japan; vol. 53; nb. 10; (1980); p. 3027 - 3028 View in Reaxys

O Na +

S O–

O

Rx-ID: 19038569 View in Reaxys 122/146 Yield

Conditions & References Reaction Steps: 4 1: methanol / 19 h / Heating 2: 1.) BuLi / 1.) THF, a.) -78 deg C, 20 min, b.) RT, 20 min, 2.) THF, from -78 deg C to RT 3: 1.) BuLi, 2.) CCl4 / 1.) THF, -78 deg C, 2.) THF, 20 min 4: 88 percent / AgClO4, CF3COOH / H2O / 1 h / Heating With tetrachloromethane, n-butyllithium, silver perchlorate, trifluoroacetic acid in methanol, water Kotake, Hiroshi; Inomata, Katsuhiko; Kinoshita, Hideki; Sakamoto, Yasuko; Kaneto, Yoko; Bulletin of the Chemical Society of Japan; vol. 53; nb. 10; (1980); p. 3027 - 3028 View in Reaxys

O S O

O

Rx-ID: 19049197 View in Reaxys 123/146 Yield

Conditions & References Reaction Steps: 2 1: 1.) BuLi, 2.) CCl4 / 1.) THF, -78 deg C, 2.) THF, 20 min 2: 88 percent / AgClO4, CF3COOH / H2O / 1 h / Heating With tetrachloromethane, n-butyllithium, silver perchlorate, trifluoroacetic acid in water Kotake, Hiroshi; Inomata, Katsuhiko; Kinoshita, Hideki; Sakamoto, Yasuko; Kaneto, Yoko; Bulletin of the Chemical Society of Japan; vol. 53; nb. 10; (1980); p. 3027 - 3028 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

53/62

2018-05-06 22:32:29

O

Rx-ID: 7160570 View in Reaxys 124/146 Yield

Conditions & References Brown,H.C. et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 2147 - 2149 View in Reaxys Mukaiyama,T. et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 4763 - 4765 View in Reaxys Tamao,K. et al.; Chemistry Letters; (1976); p. 1239 - 1242 View in Reaxys Cuvigny; Normant; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 265; (1967); p. 245 View in Reaxys Cuvigny; Normant; Bulletin de la Societe Chimique de France; (1968); p. 4990 View in Reaxys Staab; Jost; Justus Liebigs Annalen der Chemie; vol. 655; (1962); p. 90,93 View in Reaxys Araki et al.; Bulletin of the Chemical Society of Japan; vol. 47; (1974); p. 1777 View in Reaxys Kende et al.; Synthetic Communications; vol. 8; (1978); p. 59 View in Reaxys Farberov et al.; Journal of Organic Chemistry USSR (English Translation); vol. 10; (1974); p. 48,51; Zhurnal Organicheskoi Khimii; vol. 10; (1974); p. 50 View in Reaxys Gordash et al.; Journal of Organic Chemistry USSR (English Translation); vol. 11; (1975); p. 533; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 538 View in Reaxys Kosel' et al.; Uchenye Zapiski Yaroslavskogo Tekhnologicheskogo Instituta; vol. 13; (1970); p. 128,129-138; ; vol. 77; nb.

74941u; Chem. Zentralbl.; 1971 17 N 190 View in Reaxys Granito; Schultz; Journal of Organic Chemistry; vol. 28; (1963); p. 879 View in Reaxys Kraus; Patchornik; Journal of the American Chemical Society; vol. 93; (1971); p. 7325 View in Reaxys Pelter et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1976); p. 2435 View in Reaxys Villieras et al.; Synthesis; (1979); p. 968 View in Reaxys Schwartz; Cannon; Journal of the American Chemical Society; vol. 96; (1974); p. 4721 View in Reaxys Suzuki et al.; Tetrahedron Letters; (1975); p. 2195 View in Reaxys Szatajko; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 37; (1967); p. 1,21,46 View in Reaxys Achaya; Amma; Indian Journal of Chemistry; vol. 5; (1967); p. 109,110 View in Reaxys Tomson; Eesti NSV Teaduste Akadeemia Toimetised, Keemia, Geoloogia; (1966); p. 447,448-453; ; vol. 66; nb. 94734 View in Reaxys Van der Leij; Zwanenburg; Tetrahedron Letters; (1978); p. 3383 View in Reaxys Iwanowa et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 3109,3148 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

54/62

2018-05-06 22:32:29

Morcillo et al.; Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica; vol. 60; (1964); p. 199,203 View in Reaxys Viola; Madison; Tetrahedron Letters; (1977); p. 4495,4496, 4498 View in Reaxys Brown; Rogic; Journal of the American Chemical Society; vol. 91; (1969); p. 4304 View in Reaxys Gautier et al.; Bulletin de la Societe Chimique de France; (1967); p. 1554 View in Reaxys Piekarski et al.; Bulletin de la Societe Chimique de France; (1968); p. 4063 View in Reaxys Brown et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 6218 View in Reaxys Farberov et al.; Neftekhimiya; vol. 9; (1969); p. 107,114 View in Reaxys Haubenstock; Journal of Organic Chemistry; vol. 33; (1968); p. 3647 View in Reaxys

O

O OH

Rx-ID: 272224 View in Reaxys 125/146 Yield

Conditions & References With chlorobenzene Hey et al.; Journal of the Chemical Society; (1957); p. 1054,1056 View in Reaxys Erofeew et al.; ; nb. 42; (1958); p. 127,130; ; (1960); p. 4455 View in Reaxys

Cl

O

O OH

Rx-ID: 713095 View in Reaxys 126/146 Yield

Conditions & References Erofeew et al.; ; nb. 42; (1958); p. 127,130; ; (1960); p. 4455 View in Reaxys Hey et al.; Journal of the Chemical Society; (1957); p. 1054,1056 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

55/62

2018-05-06 22:32:29

N

O O

O

O

O

Rx-ID: 20112 View in Reaxys 127/146 Yield

Conditions & References Hey et al.; Journal of the Chemical Society; (1957); p. 1054,1056 View in Reaxys

O

Cl

O

O

O

O

Rx-ID: 713144 View in Reaxys 128/146 Yield

Conditions & References Hey et al.; Journal of the Chemical Society; (1957); p. 1054,1056 View in Reaxys

HO

O

Rx-ID: 22077823 View in Reaxys 129/146 Yield

Conditions & References Reaction Steps: 2

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

56/62

2018-05-06 22:32:29

1: diethyl ether; aqueous H2O2; H2SO4 2: chlorobenzene With diethyl ether, sulfuric acid, dihydrogen peroxide, chlorobenzene Hey et al.; Journal of the Chemical Society; (1957); p. 1054,1056 View in Reaxys

Li N

O

Rx-ID: 653652 View in Reaxys 130/146 Yield

Conditions & References With diethyl ether, anschliessend mit wss.H2SO4 Sumrell; Journal of Organic Chemistry; vol. 19; (1954); p. 817 View in Reaxys

Br–

+Mg

N

O

Rx-ID: 163676 View in Reaxys 131/146 Yield

Conditions & References With diethyl ether, Behandeln des Reaktionsgemisches mit wss. HCl Hauser; Humphlett; Weiss; Journal of the American Chemical Society; vol. 70; (1948); p. 426 View in Reaxys Shriner; Turner; Journal of the American Chemical Society; vol. 52; (1930); p. 1267 View in Reaxys

O

O

O

O

O

Rx-ID: 847703 View in Reaxys 132/146 Yield

Conditions & References With aluminium trichloride Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

57/62

2018-05-06 22:32:29

Cl

O

Al

O

Cl

Cl

O

O

O

Rx-ID: 7061728 View in Reaxys 133/146 Yield

Conditions & References Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys

HO

O O

Rx-ID: 22205564 View in Reaxys 134/146 Yield

Conditions & References Reaction Steps: 2 1: phosphorus trichloride / 110 - 120 °C 2: aluminium chloride With aluminium trichloride, phosphorus trichloride Simon; Bulletin des Societes Chimiques Belges; vol. 38; (1929); p. 50; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2520 View in Reaxys Reaction Steps: 2 2: AlCl3 With aluminium trichloride Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys

Br

O O

Rx-ID: 58746 View in Reaxys 135/146 Yield

Conditions & References T= 245 °C Mortenson; Spielman; Journal of the American Chemical Society; vol. 62; (1940); p. 1609 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

58/62

2018-05-06 22:32:29

1-phenyl-hexyne-(1) O

Rx-ID: 7160571 View in Reaxys 136/146 Yield

Conditions & References With ethanol, sulfuric acid, mercury(II) oxide Truchet; Annales de Chimie (Cachan, France); vol. <10>16; (1931); p. 396; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 191; (1930); p. 855 View in Reaxys Johnson; Schwartz; Jacobs; Journal of the American Chemical Society; vol. 60; (1938); p. 1882 View in Reaxys

mercury (II)-salts

acid solution

O

Rx-ID: 7160572 View in Reaxys 137/146 Yield

Conditions & References Truchet; Annales de Chimie (Cachan, France); vol. <10>16; (1931); p. 396; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 191; (1930); p. 855 View in Reaxys Johnson; Schwartz; Jacobs; Journal of the American Chemical Society; vol. 60; (1938); p. 1882 View in Reaxys O

O OH

O

O

O

O

O

O

Rx-ID: 190914 View in Reaxys 138/146

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

59/62

2018-05-06 22:32:29

Yield

Conditions & References T= 180 - 200 °C , p= 73550.8Torr Beckham; Adkins; Journal of the American Chemical Society; vol. 56; (1934); p. 2676,2678 View in Reaxys O

O

Raney nickel

O

OH

HO

O

H

O

O

Rx-ID: 7917221 View in Reaxys 139/146 Yield

Conditions & References T= 50 °C , p= 110326 - 147102Torr , Hydrogenation Sprague; Adkins; Journal of the American Chemical Society; vol. 56; (1934); p. 2669,2671 View in Reaxys

O

O

Rx-ID: 456782 View in Reaxys 140/146 Yield

Conditions & References T= 300 °C Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys

Br

O

O

Rx-ID: 22151368 View in Reaxys 141/146 Yield

Conditions & References Reaction Steps: 2 2: 300 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

60/62

2018-05-06 22:32:29

Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys

OH

NH 2

O

Rx-ID: 461746 View in Reaxys 142/146 Yield

Conditions & References With acetic acid, sodium nitrite, anschliessend Erhitzen mit Wasserdampf Tiffeneau; Levy; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1847,1851 View in Reaxys With cis-nitrous acid Tiffeneau; Levy; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 183; (1926); p. 970 View in Reaxys

N

O

Rx-ID: 22174275 View in Reaxys 143/146 Yield

Conditions & References Reaction Steps: 3 1: alcoholic NaOH-solution 2: phosphorus trichloride / 110 - 120 °C 3: aluminium chloride With sodium hydroxide, aluminium trichloride, phosphorus trichloride Simon; Bulletin des Societes Chimiques Belges; vol. 38; (1929); p. 50; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2520 View in Reaxys

HO O

Rx-ID: 22177918 View in Reaxys 144/146 Yield

Conditions & References Reaction Steps: 5 1: sulfuric acid; hydrogen bromide 2: diluted alcohol

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

61/62

2018-05-06 22:32:29

3: alcoholic NaOH-solution 4: phosphorus trichloride / 110 - 120 °C 5: aluminium chloride With sodium hydroxide, aluminium trichloride, ethanol, sulfuric acid, hydrogen bromide, phosphorus trichloride Simon; Bulletin des Societes Chimiques Belges; vol. 38; (1929); p. 50; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2520 View in Reaxys

OH

O N

OH

NH 2

O

Rx-ID: 7981367 View in Reaxys 145/146 Yield

Conditions & References Tiffeneau; Levy; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 183; (1926); p. 970 View in Reaxys

O

HO

HO

O O

Rx-ID: 758009 View in Reaxys 146/146 Yield

Conditions & References T= 400 - 450 °C , durch Ueberleiten ueber MnO Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 833 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

62/62

2018-05-06 22:32:29